Enantioselective Synthesis of Alcohols and Amines: The Ichikawa Synthesis of (+)-Geranyllinaloisocyanide

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Allylic Alcohol ◽  
Florida State University ◽  
State University ◽  
Quaternary Amine ◽  
National University ◽  
Cu Catalyst ◽  
Enantioselective Addition ◽  
Institute Of Technology ◽  
The University ◽  
University Of Manchester

Shuichi Nakamura of the Nagoya Institute of Technology reduced (Angew. Chem. Int. Ed. 2011, 50, 2249) the α-oxo ester 1 to 2 with high ee. Günter Helmchen of the Universität-Heidelberg optimized (J. Am. Chem. Soc. 2011, 133, 2072) the Ir*-catalyzed rearrangement of 3 to the allylic alcohol 4. D. Tyler McQuade of Florida State University effected (J. Am. Chem. Soc. 2011, 133, 2410) the enantioselective allylic substitution of 5 to give the secondary allyl boronate, which was then oxidized to 6. Kazuaki Kudo of the University of Tokyo developed (Org. Lett. 2011, 13, 3498) the tandem oxidation of the aldehyde 7 to the α-alkoxy acid 8. Takashi Ooi of Nagoya University prepared (Synlett 2011, 1265) the secondary amine 10 by the enantioselective addition of an aniline to the nitroalkene 9. Yixin Lu of the National University of Singapore assembled (Org. Lett. 2011, 13, 2638) the α-quaternary amine 13 by the addition of the aldehyde 11 to the azodicarboxylate 10. Chan-Mo Yu of Sungkyunkwan University added (Chem. Commun. 2011, 47, 3811) the enantiomerically pure 2-borylbutadiene 15 to the aldehyde 14 to give 16 in high ee. Because the allene is readily dragged out to the terminal alkyne, this is also a protocol for the enantioselective homopropargylation of an aldehyde. Lin Pu of the University of Virginia devised (Angew. Chem. Int. Ed. 2011, 50, 2368) a protocol for the enantioselective addition of 17 to the aldehyde 18 to give 19. Xiaoming Feng of Sichuan University developed (Angew. Chem. Int. Ed. 2011, 50, 2573) a Mg catalyst for the enantioselective addition of 21 to the α-oxo ester 20. Tomonori Misaka and Takashi Sugimura of the University of Hyogo added (J. Am. Chem. Soc. 2011, 133, 5695) 23 to 24 to give the Z-amide 25 in high ee. Marc L. Snapper and Amir H. Hoveyda of Boston College developed (J. Am. Chem. Soc. 2011, 133, 3332) a Cu catalyst for the enantioselective allylation of the imine 26. Jonathan Clayden of the University of Manchester effected (Org. Lett. 2010, 12, 5442) the enantioselective rearrangement of the amide 29 to the α-quaternary amine 30.

Enantioselective Construction of Alkylated Centers: The Shishido Synthesis of (+)-Helianane

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Allylic Alcohol ◽  
National University ◽  
Cu Catalyst ◽  
Rh Catalyst ◽  
Enantioselective Acylation ◽  
Enantioselective Addition ◽  
Institute Of Technology ◽  
Enantioselective Alkylation ◽  
Seoul National University ◽  
The University

Teck-Peng Loh of Nanyang Technological University developed (Org. Lett. 2011, 13, 876) a catalyst for the enantioselective addition of an aldehyde to the versatile acceptor 2 to give 3. Kirsten Zeitler of the Universität Regensburg employed (Angew. Chem. Int. Ed. 2011, 50, 951) a complementary strategy for the enantioselective coupling of 4 with 5. Clark R. Landis of the University of Wisconsin devised (Org. Lett. 2011, 13, 164) an Rh catalyst for the enantioselective formylation of the diene 7. Don M. Coltart of Duke University alkylated (J. Am. Chem. Soc. 2011, 133, 8714) the chiral hydrazone of acetone to give 9, then alkylated again to give, after hydrolysis, the ketone 11 in high ee. Youming Wang and Zhenghong Zhou of Nankai University effected (J. Org. Chem. 2011, 76, 3872) the enantioselective addition of acetone to the nitroalkene 12. Takeshi Ohkuma of Hokkaido University achieved (Angew. Chem. Int. Ed. 2011, 50, 5541) high ee in the Ru-catalyzed hydrocyanation of 15. Gregory C. Fu, now at the California Institute of Technology, coupled (J. Am. Chem. Soc. 2011, 133, 8154) the 9-BBN borane 18 with the racemic chloride 17 to give 19 in high ee. Scott McN. Sieburth of Temple University optimized (Org. Lett. 2011, 13, 1787) an Rh catalyst for the enantioselective intramolecular hydrosilylation of 20 to 21. Several general methods have been devised for the enantioselective assembly of quaternary alkylated centers. Sung Ho Kang of KAIST Daejon developed (J. Am. Chem. Soc. 2011, 133, 1772) a Cu catalyst for the enantioselective acylation of the prochiral diol 22. Hyeung-geun Park of Seoul National University established (J. Am. Chem. Soc. 2011, 133, 4924) a phase transfer catalyst for the enantioselective alkylation of 24. Peter R. Schreiner of Justus-Liebig University Giessen found (J. Am. Chem. Soc. 2011, 133, 7624) a silicon catalyst that efficiently rearranged the Shi-derived epoxide of 26 to the aldehyde 27. Amir H. Hoveyda of Boston College coupled (J. Am. Chem. Soc. 2011, 133, 4778) 28 with the alkynyl Al reagent 29 to give 30 in high ee. Kozo Shishido of the University of Tokushima prepared (Synlett 2011, 1171) 31 by the Mitsunobu coupling of m-cresol with the enantiomerically pure allylic alcohol.

Enantioselective Synthesis of Alcohols and Amines: The Zhu Synthesis of (+)-Trigonoliimine A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Secondary Alcohol ◽  
Allylic Alcohol ◽  
Princeton University ◽  
Terminal Alkene ◽  
National University ◽  
Amino Amide ◽  
Enantioselective Epoxidation ◽  
Enantioselective Addition ◽  
Institute Of Technology ◽  
The University

The enantioselective epoxidation of a terminal alkene 1 has been a long-sought goal of organic synthesis. Albrecht Berkessel of the University of Cologne devised (Angew. Chem. Int. Ed. 2013, 52, 8467) a Ti catalyst that mediated the conversion of 1 to 2. Zhi Li of the National University of Singapore described (Chem. Commun. 2013, 49, 11572) a cell-based system that effected the enantioselective epoxidation of 3 to 4. Antonio Mezzetti of ETH Zürich and Francesco Santoro of Firmenich SA car­ried out (Angew. Chem. Int. Ed. 2013, 52, 10352) the enantioselective hydrogena­tion of 5 to the allylic alcohol 6. Elena Fernández of the Universitat Rovira i Virgilli and Andrew Whiting of Durham University devised (Org. Lett. 2013, 15, 4810) a protocol for the enantioselective conjugate borylation of the imine derived from 7, leading to the secondary alcohol 8. Benjamin List of the Max-Planck-Institute für Kohlenforschung, Mülheim and Choong Eui Song of Sungkyunkwan University con­densed (Angew. Chem. Int. Ed. 2013, 52, 12143) the thioester 10 with the aldehyde 9 to give the alcohol 11. Toshiro Harada of the Kyoto Institute of Technology developed (Org. Lett. 2013, 15, 4198) a general procedure for the enantioselective addition of a terminal alkene 12 to an aldehyde 9. As illustrated by the preparation of 13, this appears to be tolerant of a variety of organic functional groups. Professor Harada also established (Chem. Eur. J. 2013, 19, 17707) a protocol for the enantioselective addition of an alkyne 14 to an aldehyde to give the branched product 15. Chun-Jiang Wang and Xumu Zhang of Wuhan University hydrogenated (Angew. Chem. Int. Ed. 2013, 52, 8416) the alkyne 16 to the protected allylic amine 17. Keiji Maruoka of Kyoto University effected (J. Am. Chem. Soc. 2013, 135, 18036) the enantioselective α-amination of an aldehyde 18, to give 19. David W. C. MacMillan of Princeton University described (J. Am. Chem. Soc. 2013, 135, 11521) a comple­mentary approach, not illustrated. David J. Fox of the University of Warwick reduced (Chem. Commun. 2013, 49, 10022) the ketone 20, then rearranged the resulting sec­ondary alcohol to the α-amino amide 21.

Stereocontrolled C-O Ring Construction: The Fuwa/Sasaki Synthesis of Attenol A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Gold Catalysis ◽  
Membered Ring ◽  
Allylic Alcohol ◽  
State University ◽  
Prins Cyclization ◽  
University Of Florida ◽  
University Of Pittsburgh ◽  
Colorado State University ◽  
Institute Of Technology ◽  
The University

Since five-membered ring ethers often do not show good selectivity on equilibration, single diastereomers are best formed under kinetic control. Aaron Aponick of the University of Florida demonstrated (Organic Lett. 2008, 10, 669) that under gold catalysis, the allylic alcohol 1 cyclized to 2 with remarkable diastereocontrol. Six-membered rings also formed with high cis stereocontrol. Ian Cumpstey of Stockholm University showed (Chem. Commun. 2008, 1246) that with protic acid, allylic acetates such as 3 cyclized with clean inversion at the allylic center, and concomitant debenzylation. J. Stephen Clark of the University of Glasgow found (J. Org. Chem. 2008, 73, 1040) that Rh catalyzed cyclization of 5 proceeded with high selectivity for insertion into Ha, leading to the alcohol 6. Saumen Hajra of the Indian Institute of Technology, Kharagpur took advantage (J. Org. Chem. 2008, 73, 3935) of the reactivity of the aldehyde of 7, effecting selective addition of 7 to 8, to deliver, after reduction, the lactone 9. Tomislav Rovis of Colorado State University observed (J. Org. Chem. 2008, 73, 612) that 10 could be cyclized selectively to either 11 or 12. Nadège Lubin-Germain, Jacques Uziel and Jacques Augé of the University of Cergy- Pontoise devised (Organic Lett. 2008, 10, 725) conditions for the indium-mediated coupling of glycosyl fluorides such as 13 with iodoalkynes such as 14 to give the axial C-glycoside 15. Katsukiyo Miura and Akira Hosomi of the University of Tsukuba employed (Chemistry Lett. 2008, 37, 270) Pt catalysis to effect in situ equilibration of the alkene 16 to the more stable regioisomer. Subsequent condensation with the aldehyde 17 led via Prins cyclization to the ether 18. Paul E. Floreancig of the University of Pittsburgh showed (Angew. Chem. Int. Ed. 2008, 47, 4184) that Prins cyclization could be also be initiated by oxidation of the benzyl ether 19 to the corresponding carbocation. Chan-Mo Yu of Sungkyunkwan University developed (Organic Lett. 2008, 10, 265) a stereocontrolled route to seven-membered ring ethers, by Pd-mediated stannylation of allenes such as 21, followed by condensation with an aldehyde.

Other Methods for Carbocyclic Construction: The Porco Synthesis of (-)-Hyperibone K

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Oxidative Cyclization ◽  
Florida State University ◽  
State University ◽  
Colorado State University ◽  
Intramolecular Alkylation ◽  
University Of Wisconsin ◽  
Tokyo Institute ◽  
Institute Of Technology ◽  
University Of Bristol ◽  
The University

Varinder K. Aggarwal of the University of Bristol described (Angew. Chem. Int. Ed. 2010, 49, 6673) the conversion of the Sharpless-derived epoxide 1 into the cyclopropane 2. Christopher D. Bray of Queen Mary University of London established (Chem. Commun. 2010, 46, 5867) that the related conversion of 3 to 5 proceeded with high diastereocontrol. Javier Read de Alaniz of the University of California, Santa Barbara, extended (Angew. Chem. Int. Ed. 2010, 49, 9484) the Piancatelli rearrangement of a furyl carbinol 6 to allow inclusion of an amine 7, to give 8. Issa Yavari of Tarbiat Modares University described (Synlett 2010, 2293) the dimerization of 9 with an amine to give 10. Jeremy E. Wulff of the University of Victoria condensed (J. Org. Chem. 2010, 75, 6312) the dienone 11 with the commercial butadiene sulfone 12 to give the highly substituted cyclopentane 13. Robert M. Williams of Colorado State University showed (Tetrahedron Lett. 2010, 51, 6557) that the condensation of 14 with formaldehyde delivered the cyclopentanone 15 with high diastereocontrol. D. Srinivasa Reddy of Advinus Therapeutics devised (Tetrahedron Lett. 2010, 51, 5291) conditions for the tandem conjugate addition/intramolecular alkylation conversion of 16 to 17. Marie E. Krafft of Florida State University reported (Synlett 2010, 2583) a related intramolecular alkylation protocol. Takao Ikariya of the Tokyo Institute of Technology effected (J. Am. Chem. Soc. 2010, 132, 11414) the enantioselective Ru-mediated hydrogenation of bicyclic imides such as 18. This transformation worked equally well for three-, four-, five-, six-, and seven-membered rings. Stefan France of the Georgia Institute of Technology developed (Org. Lett. 2010, 12, 5684) a catalytic protocol for the homo-Nazarov rearrangement of the doubly activated cyclopropane 20 to the cyclohexanone 21. Richard P. Hsung of the University of Wisconsin effected (Org. Lett. 2010, 12, 5768) the highly diastereoselective rearrangement of the triene 22 to the cyclohexadiene 23. Strategies for polycyclic construction are also important. Sylvain Canesi of the Université de Québec devised (Org. Lett. 2010, 12, 4368) the oxidative cyclization of 24 to 25.

Functional Group Transformations

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Gold Catalyst ◽  
Sulfonyl Chloride ◽  
Allylic Alcohol ◽  
West Virginia University ◽  
Israel Institute ◽  
University Of Texas ◽  
Amino Amide ◽  
Cu Catalyst ◽  
Institute Of Technology ◽  
The University

Mark Gandelman of the Technion–Israel Institute of Technology devised (Adv. Synth. Catal. 2011, 353, 1438) a protocol for the decarboxylative conversion of an acid 1 to the iodide 3. Doug E. Frantz of the University of Texas, San Antonio effected (Angew. Chem. Int. Ed. 2011, 50, 6128) conversion of a β-keto ester 4 to the diene 5 by way of the vinyl triflate. Pei Nian Liu of the East China University of Science and Technology and Chak Po Lau of the Hong Kong Polytechnic University (Adv. Synth. Catal. 2011, 353, 275) and Robert G. Bergman and Kenneth N. Raymond of the University of California, Berkeley (J. Am. Chem. Soc. 2011, 133, 11964) described new Ru catalysts for the isomerization of an allylic alcohol 6 to the ketone 7. Xiaodong Shi of West Virginia University optimized (Adv. Synth. Catal. 2011, 353, 2584) a gold catalyst for the rearrangement of a propargylic ester 8 to the enone 9. Xue-Yuan Liu of Lanzhou University used (Adv. Synth. Catal. 2011, 353, 3157) a Cu catalyst to add the chloramine 11 to the alkyne 10 to give 12. Kasi Pitchumani of Madurai Kamaraj University converted (Org. Lett. 2011, 13, 5728) the alkyne 13 into the α-amino amide 15 by reaction with the nitrone 14. Katsuhiko Tomooka of Kyushu University effected (J. Am. Chem. Soc. 2011, 133, 20712) hydrosilylation of the propargylic ether 16 to the alcohol 17. Matthew J. Cook of Queen’s University Belfast (Chem. Commun. 2011, 47, 11104) and Anna M. Costa and Jaume Vilarrasa of the Universitat de Barcelona (Org. Lett. 2011, 13, 4934) improved the conversion of an alkenyl silane 18 to the iodide 19. Vinay Girijavallabhan of Merck/Kenilworth developed (J. Org. Chem. 2011, 76, 6442) a Co catalyst for the Markovnikov addition of sulfide to an alkene 20. Hojat Veisi of Payame Noor University oxidized (Synlett 2011, 2315) the thiol 22 directly to the sulfonyl chloride 23. Nicholas M. Leonard of Abbott Laboratories prepared (J. Org. Chem. 2011, 76, 9169) the chromatography-stable O-Su ester 25 from the corresponding acid 24.

Ian Gordon Ross 1926 - 2006

2009 ◽  
Vol 20 (1) ◽  
pp. 91 ◽  
Author(s):  
Gad Fischer ◽  
Robert G. Gilbert
Keyword(s):  
Driving Force ◽  
Electronic Spectroscopy ◽  
Florida State University ◽  
State University ◽  
Vice Chancellor ◽  
Pi Systems ◽  
National University ◽  
University College London ◽  
Postdoctoral Research ◽  
The University

Ian Gordon Ross (1926?2006) was educated at the University of Sydney (BSc 1943?1946, MSc 1947?1949) and University College London (PhD 1949?1952), did postdoctoral research at Florida State University (1953?1954), and was a staff member at the University of Sydney, 1954?1967. In 1968, he moved to the Australian National University (ANU) as Professor of Chemistry, where he also became Dean of Science (1973), Deputy Vice-Chancellor (1977) and Pro-Vice-Chancellor (Special Projects) (1989?1990). He was instrumental in setting up Anutech, the commercial arm of the University. He was a driving force behind the establishment of undergraduate and postgraduate engineering at the ANU. His research centred on electronic spectroscopy of pi systems.

Transition Metal-Mediated Ring Construction: The Yu Synthesis of 1-Desoxyhypnophilin

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Transition Metal ◽  
Quinone Methide ◽  
Michigan State University ◽  
State University ◽  
Enantiomerically Pure ◽  
Quaternary Centers ◽  
University Of Oxford ◽  
National University ◽  
Cu Catalyst ◽  
The University

Both 1 and 3 are inexpensive prochiral starting materials. Tae-Jong Kim of Kyungpook National University devised (Organomet. 2008, 27, 1026) a chiral Cu catalyst that efficiently converted 1 (other ring sizes worked as well) to the enantiomerically pure ester 2. Alexandre Alexakis of the University of Geneva found (Adv. Synth. Cat. 2008, 350, 1090) a chiral Cu catalyst that mediated the enantioselective coupling of 3 with Grignard reagents such as 4 . The π-allyl Pd complex derived from 6 is also prochiral. Barry M. Trost of Stanford University showed (Angew. Chem. Int. Ed. 2008, 47, 3759) that with appropriate ligand substitution, coupling with the phthalimide 7 proceeded to give 8, readily convertible to (-)-oseltamivir (Tamiflu) 9, in high ee. Jonathan W. Burton of the University of Oxford found (Chem Commun. 2008, 2559) that Mn(OAc)3 -mediated cyclization of 10 delivered the lactone 12 with high diastereocontrol. John Montgomery of the University of Michigan observed (Organic Lett. 2008, 10, 811) that the Ni-catalyzed cyclization of 12 also proceeded with high diastereocontrol. Ken Tanaka of the Tokyo University of Agriculture and Technology combined (Angew. Chem. Int. Ed. 2008, 47, 1312) Rh-catalyzed ene-yne cyclization of 14 with catalytic ortho C-H functionalization, leading to 16 in high ee. Eric N. Jacobsen of Harvard University designed (Angew. Chem. Int. Ed. 2008, 47, 1469) a chiral Cr catalyst for the intramolecular carbonyl ene reaction, that converted 17 to 18 in high ee. Using a stoichiometric prochiral Cr carbene complex 20 and the enantiomerically-pure secondary propargylic ether 19, Willam D. Wulff of Michigan State University prepared (J. Am. Chem. Soc. 2008, 130, 2898) a facially-selective Cr-complexed o -quinone methide intermediate, that cyclized to 21 with high ee. A variety of methods have been put forward for the transition metal-mediated construction of polycarbocyclic systems. One of the more powerful is the enantioselective Rh-catalyzed stitching of the simple substrate 22 into the tricycle 23 devised (J. Am. Chem. Soc. 2008, 130, 3451) by Takanori Shibata of Waseda University. Inter alia, ozonolysis of 23 delivered the cyclopentane 24 containing two all-carbon quaternary centers.

Substituted Benzenes: The Gu Synthesis of Rhazinal

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Aryl Halide ◽  
Indian Institute ◽  
University Of California ◽  
University Of Pennsylvania ◽  
Ru Catalyst ◽  
Cu Catalyst ◽  
Institute Of Technology ◽  
The University ◽  
University Of Manchester ◽  
Structure Of Matter

Sisir K. Mandal of Asian Paints R&T Centre, Mumbai used (Tetrahedron Lett. 2013, 54, 530) a Ru catalyst to couple 2 with an electron-rich arene 1 to give 3. Jun-ichi Yoshida of Kyoto University (J. Am. Chem. Soc. 2013, 135, 5000) and John F. Hartwig of the University of California, Berkeley (J. Am. Chem. Soc. 2013, 135, 8480) also reported direct amination protocols. Tommaso Marcelli of the Politecnico di Milano and Michael J. Ingleson of the University of Manchester effected (J. Am. Chem. Soc. 2013, 135, 474) the electrophilic borylation of the aniline 4 to give 5. The regioselectivity of Ir-catalyzed borylation (J. Am. Chem. Soc. 2013, 135, 7572; Org. Lett. 2013, 15, 140) is complementary to the electrophilic process. Professor Hartwig carried (Angew. Chem. Int. Ed. 2013, 52, 933) the borylated product from 6 onto Ni-mediated coupling to give the alkylated product 7. Weiping Su of the Fujian Institute of Research on the Structure of Matter devised (Org. Lett. 2013, 15, 1718) an intriguing Pd-mediated oxidative coupling of nitroethane 9 with 8 to give 10. The coupling is apparently not proceeding via nitroethylene. Peiming Gu of Ningxia University developed (Org. Lett. 2013, 15, 1124) an azide-based cleavage that converted the aldehyde 11 into the formamide 13. Zhong-Quan Liu of Lanzhou University showed (Tetrahedron Lett. 2013, 54, 3079) that an aromatic carboxylic acid 14 could be oxidatively decarboxylated to the chloride 15. Gérard Cahiez of the Université Paris 13 found (Adv. Synth. Catal. 2013, 355, 790) mild Cu-catalyzed conditions for the reductive decarboxylation of aromatic carboxylic acids, and Debabrata Maiti of the Indian Institute of Technology, Mumbai found (Chem. Commun. 2013, 49, 252) Pd-mediated conditions for the dehydroxymethylation of benzyl alcohols (neither illustrated). Pravin R. Likhar of the Indian Institute of Chemical Technology prepared (Adv. Synth. Catal. 2013, 355, 751) a Cu catalyst that effected Castro-Stephens coupling of 16 with 17 at room temperature. Arturo Orellana of York University (Chem. Commun. 2013, 49, 5420) and Patrick J. Walsh of the University of Pennsylvania (Org. Lett. 2013, 15, 2298) showed that a cyclopropanol 20 can couple with an aryl halide 19 to give 21.

Construction of Alkylated Stereogenic Centers

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Phase Transfer ◽  
Conjugate Addition ◽  
Enantioselective Hydrogenation ◽  
Boronic Acids ◽  
National University ◽  
Cu Catalyst ◽  
Institute Of Technology ◽  
Enantioselective Alkylation ◽  
Seoul National University ◽  
The University

Andreas Pfaltz of the University of Basel and Keisuke Suzuki of the Tokyo Institute of Technology showed (Angew. Chem. Int. Ed. 2010, 49, 881) that the iodohydrin of 1 did not interfere with the enantioselective hydrogenation. J. R. Falck of UT Southwestern developed (J. Am. Chem. Soc. 2010, 132, 2424) a procedure for coupling arene boronic acids with a cyano triflate 3, readily available in high ee from the corresponding aldehyde. Anita R. Maguire of University College Cork devised (J. Am. Chem. Soc. 2010, 132, 1184) a Cu catalyst for the enantioselective C-H insertion cyclization of 5 to 6. Jin-Quan Yu of Scripps/La Jolla established (J. Am. Chem. Soc. 2010, 132, 460) a complementary enantioselective C-H functionalization protocol, converting the prochiral 7 into 8 in high ee. Xumu Zhang of Rutgers University effected (Angew. Chem. Int. Ed. 2010, 49, 4047) enantioselective branching hydroformylation of 9 to give 10. T. V. RajanBabu of Ohio State University established (J. Am. Chem. Soc. 2010, 132, 3295) the enantioselective hydrovinylation of a diene 11 to the diene 12. Gregory C. Fu extended (J. Am. Chem. Soc. 2010, 132, 1264, 5010) Ni-mediated cross-coupling, both with alkenyl and aryl nucleophiles, to the racemic bromoketone 13. Hyeung-geun Park and Sang-sup Jew of Seoul National University used (Organic Lett. 2010, 12 , 2826) their asymmetric phase transfer protocol to effect the enantioselective alkylation of the amide 15. Kyung Woon Jung of the University of Southern California showed (J. Org. Chem. 2010, 75, 95) that the oxidative Pd-mediated Heck coupling of arene boronic acids to 17 could be effected in high ee. Nicolai Cramer of ETH Zurich observed (J. Am. Chem. Soc. 2010, 132, 5340) high enantioinduction in the cleavage of the prochiral cyclobutanol 19. Alexandre Alexakis of the University of Geneva achieved (Organic Lett. 2010, 12, 1988) the long-sought goal of efficient enantioselective conjugate addition of a Grignard reagent to an unsaturated aldehyde 21. Professor Alexakis also established (Organic Lett. 2010, 12, 2770) conditions for enantioselective conjugate addition to a nitrodiene 23. This procedure worked equally well for β-alkynyl nitroalkenes.

New Methods for C-N Ring Construction

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
New York ◽  
Gold Complex ◽  
Cascade Process ◽  
State University ◽  
University Of Alberta ◽  
Cornell University ◽  
University Of New Mexico ◽  
Memory Of Chirality ◽  
Cu Catalyst ◽  
The University

Chaozhong Li of the Shanghai Institute of Organic Chemistry demonstrated (Organic Lett. 2008, 10, 4037) facile and selective Cu-catalyzed β-lactam formation, converting 1 to 2. Paul Helquist of the University of Notre Dame devised (Organic Lett. 2008, 10, 3903) an effective catalyst for intramolecular alkyne hydroamination, converting 3 into the imine 4. Six-membered ring construction worked well also. Jon T. Njardarson of Cornell University found (Organic Lett. 2008, 10, 5023) a Cu catalyst for the rearrangement of alkenyl aziridines such as 5 to the pyrroline 6. Philippe Karoyan of the UPMC, Paris developed (J. Org. Chem. 2008, 73, 6706) an interesting chiral auxiliary directed cascade process, converting the simple precursor 7 into the complex pyrrolidine 9. Sherry R. Chemler of the State University of New York, Buffalo devised (J. Am. Chem. Soc. 2008, 130, 17638) a chiral Cu catalyst for the cyclization of 10, to give 12 with substantial enantiocontrol. Wei Wang of the University of New Mexico demonstrated (Chem. Commun. 2008, 5636) the organocatalyzed condensation of 13 and 14 to give 16 with high enantio- and diastereocontrol. Two complementary routes to azepines/azepinones have appeared. F. Dean Toste of the University of California, Berkeley showed (J. Am. Chem. Soc. 2008, 130, 9244) that a gold complex catalyzed the condensation of 17 and 18 to give 19. Frederick G. West of the University of Alberta found (Organic Lett. 2008, 10, 3985) that lactams such as 20 could be ring-expanded by the addition of the propiolate anion 21. Takeo Kawabata of Kyoto University extended (Organic Lett . 2008, 10, 3883) “memory of chirality” studies to the cyclization of 23, demonstrating that 24 was formed in high ee. Paul V. Murphy of University College Dublin took advantage (Organic Lett . 2008, 10, 3777) of the well-known intramolecular addition of azides to alkenes, showing that the intermediate could be intercepted with nucleophiles such as thiophenol, to give the cyclized product 26 with high diastereocontrol.

Sign in / Sign up

Export Citation Format

Share Document