Metal-Mediated Carbocyclic Construction: The Simpkins Synthesis of Ialibinones A and B

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Gold Catalyst ◽  
Conjugate Addition ◽  
South Florida ◽  
Pt Catalyst ◽  
General Strategy ◽  
Ru Catalyst ◽  
University Of Technology ◽  
Rh Catalyst ◽  
Institute Of Technology ◽  
The University

Adriaan J. Minnaard and Ben L. Feringa of the University of Groningen devised (J. Am. Chem. Soc. 2010, 132, 14349) what promises to be a general strategy for the construction of enantiomerically pure cyclopropanes, based on conjugate addition to acceptors such as 1 . X. Peter Zhang of the University of South Florida developed (J. Am. Chem. Soc. 2010, 132, 12796) a Co catalyst for the enantioselective cyclopropanation of α-olefins such as 3. Seiji Iwasa of Toyohashi University of Technology designed (Angew. Chem. Int. Ed. 2010, 49, 8439) a resin-bound Ru catalyst that could be used repeatedly for the enantioselective cyclization of the ester 6. Rai-Shung Lin of National Tsing-Hua University showed (Angew. Chem. Int. Ed. 2010, 49, 9891) that a gold catalyst could expand the alkyne 8 to the cyclobutene 9. Takao Ikariya of the Tokyo Institute of Technology reported (J. Am. Chem. Soc. 2010, 132, 16637) a detailed study of the enantioselective conjugate addition of malonate 11 to cyclopentenone 10. Vladimir A. D’yakonov of the Russian Academy of Sciences, Ufa, showed (Tetrahedron Lett. 2010, 51, 5886) that a cyclic alkyne 13 could be annulated to the cyclopentenone 14. Shunichi Hashimoto of Hokkaido University also designed (Angew. Chem. Int. Ed. 2010, 49, 6979) a resin-bound Rh catalyst that could also be used repeatedly for the enantioselective cyclization of the ester 15. Tushar Kanti Chakraborty of the Central Drug Research Institute used (Tetrahedron Lett. 2010, 51, 4425) Ti(III) to mediate the diastereoselective cyclization of 17 to 18. Alexandre Alexakis of the University of Geneva extended (Synlett 2010, 1694) enantioselective conjugate addition of isopropenyl to the more difficult enone 19. Joseph P. A. Harrity of the University of Sheffield showed (Org. Lett. 2010, 12, 4832) that Pd could catalyze the rearrangement of 21 to 22. Strategies for the controlled construction of polycyclic ring systems are also important. Günter Helmchen of the Universität Heidelberg showed (J. Org. Chem. 2010, 75, 7917) that 23 was efficiently cyclized to the diene with Pt catalyst. The reaction could be carried out in the presence of the dienophile 24 to give 25 directly.

Transition Metal-Mediated Construction of Carbocycles: Dimethyl Gloiosiphone A (Takahashi), Pasteurestin A (Mulzer), and Pentalenene (Fox)

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Transition Metal ◽  
South Florida ◽  
Health Science ◽  
Pt Catalyst ◽  
Max Planck ◽  
Au Catalyst ◽  
Ru Catalyst ◽  
National University ◽  
Rh Catalyst ◽  
The University

There continue to be new developments in transition metal- and lanthanide-mediated construction of carbocycles. Although a great deal has been published on the asymmetric cyclopropanation of styrene, relatively little had been reported for other classes of alkenes. Tae-Jeong Kim of Kyungpook National University has devised (Tetrahedron Lett. 2007, 48, 8014) a Ru catalyst for the cyclopropanation of simple α-olefins such as 1. X. Peter Zhang of the University of South Florida has developed (J. Am.Chem. Soc. 2007, 129, 12074) a Co catalyst for the cyclopropanation of alkenes such as 5 having electron-withdrawing groups. Alexandre Alexakis of the Université de Genève has reported(Angew. Chem. Int. Ed. 2007, 46, 7462) simple monophosphine ligands that enabled enantioselective conjugate addition to prochiral enones, even difficult substrates such as 8. Seunghoon Shin of Hanyang University has found (Organic Lett. 2007, 9, 3539) an Au catalyst that effected the diastereoselective cyclization of 10 to the cyclohexene 11, and Radomir N. Saicic of the University of Belgrade has carried out (Organic Lett. 2007, 9, 5063), via transient enamine formation, the diastereoselective cyclization of 12 to the cyclohexane 13. Alois Fürstner of the Max-Planck- Institut, Mülheim has devised (J. Am. Chem. Soc. 2007, 129, 14836) a Rh catalyst that cyclized the aldehyde 14 to the cycloheptenone 15. Some of the most exciting investigations reported in recent months have been directed toward the direct diastereo- and enantioselective preparation of polycarbocyclic products. Rai-Shung Liu of National Tsing-Hua University has extended (J. Org. Chem. 2007, 72, 567) the intramolecular Pauson-Khand cyclization to the epoxy enyne 16, leading to the 5-5 product 17. Michel R. Gagné of the University of North Carolina has devised (J. Am. Chem. Soc. 2007, 129, 11880) a Pt catalyst that smoothly cyclized the polyene 18 to the 6-6 product 19. Yoshihiro Sato of Hokkaido University and Miwako Mori of the Health Science University of Hokkaido have described (J. Am. Chem. Soc. 2007, 129, 7730) a Ru catalyst for the cyclization of 20 to the 5-6-5 product 21. Each of these processes proceeded with high diastereocontrol.

Heteroaromatic Construction: The Li Synthesis of Mycoleptodiscin A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Chemical Biology ◽  
Gold Catalyst ◽  
Indian Institute ◽  
Pd Catalyst ◽  
West Virginia University ◽  
University Of Technology ◽  
Complementary Approach ◽  
Institute Of Technology ◽  
Simple Exposure ◽  
The University

Kyungsoo Oh of Chung-Ang University cyclized (Org. Lett. 2015, 17, 450) the chloro enone 1 with NBS to the furan 2. Hongwei Zhou of Zhejiang University acylated (Adv. Synth. Catal. 2015, 357, 389) the imine 3, leading to the furan 4. H. Surya Prakash Rao of Pondicherry University found (Synlett 2014, 26, 1059) that under Blaise conditions, exposure of 5 to three equivalents of 6 led to the pyrrole 7. Yoshiaki Nishibayashi of the University of Tokyo and Yoshihiro Miyake, now at Nagoya University, prepared (Chem. Commun. 2014, 50, 8900) the pyrrole 10 by adding the silane 9 to the enone 8. Barry M. Trost of Stanford University developed (Org. Lett. 2015, 17, 1433) the phosphine-mediated cyclization of 11 to an intermediate that on brief exposure to a Pd catalyst was converted to the pyridine 12. Nagatoshi Nishiwaki of the Kochi University of Technology added (Chem. Lett. 2015, 44, 776) the dinitrolactam 14 to the enone 13 to give the pyridine 15. Metin Balci of the Middle East Technical University assembled (Org. Lett. 2015, 17, 964) the tricyclic pyridine 18 by adding propargyl amine 17 to the aldehyde 16. Chada Raji Reddy of the Indian Institute of Chemical Technology cyclized (Org. Lett. 2015, 17, 896) the azido enyne 19 to the pyridine 20 by simple exposure to I2. Björn C. G. Söderberg of West Virginia University used (J. Org. Chem. 2015, 80, 4783) a Pd catalyst to simultaneously reduce and cyclize 21 to the indole 22. Ranjan Jana of the Indian Institute of Chemical Biology effected (Org. Lett. 2015, 17, 672) sequential ortho C–H activation and cyclization, adding 23 to 24 to give the 2-substituted indole 25. In a complementary approach, Debabrata Maiti of the Indian Institute of Technology Bombay added (Chem. Eur. J. 2015, 21, 8723) 27 to 26 to give the 3-substituted indole 28. In a Type 8 construction, Nobutaka Fujii and Hiroaki Ohno of Kyoto University employed (Chem. Eur. J. 2015, 21, 1463) a gold catalyst to add 30 to 29, leading to 31.

C–H Functionalization

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Oxidative Cyclization ◽  
South Florida ◽  
Hypervalent Iodine ◽  
Direct Oxidation ◽  
University Of Texas ◽  
Ru Catalyst ◽  
University Of Technology ◽  
National University ◽  
Indian Institute Of Science ◽  
The University

Masayuki Inoue of the University of Tokyo oxidized (Tetrahedron Lett. 2011, 52, 4654) the alkyl benzene 1 to the nitrate 2, which could be carried on to the amide 5, the nitrile 6, the alcohol 7, or the azide 8. X. Peter Zhang of the University of South Florida developed (Chem. Sci. 2012, 2, 2361) a Co catalyst for the cyclization of 7 to 8. Justin Du Bois of Stanford University reported (J. Am. Chem. Soc. 2011, 133, 17207) the oxidative cyclization of the sulfamate corresponding to 7 using a Ru catalyst. Seongmin Lee of the University of Texas showed (Org. Lett. 2011, 13, 4766) that the oxidative cyclization of 9 gave the amine 10 with high diastereoselectivity. Fabrizio Fabris of the Università di Venezia used (Tetrahedron Lett. 2011, 52, 4478) a Ru catalyst to oxidize 11 to the ketone 12. Ying-Yeung Yeung of the National University of Singapore found (Org. Lett. 2011, 13, 4308) that hypervalent iodine was sufficient to oxidize 13 to the ketone 14. Huanfeng Jiang of the South China University of Technology methoxycarbonylated (Chem. Commun. 2011, 47, 12224) 15 under Pd catalysis to give 16. Professor Inoue found (Org. Lett. 2011, 13, 5928) that the oxidative cyanation of 17 proceeded with high diastereoselectivity to give 18. Mamoru Tobisu and Naoto Chatani of Osaka University activated (J. Am. Chem. Soc. 2011, 133, 12984) 19 with a Pd catalyst to enable coupling with 20 to give 21. Rh-mediated intramolecular insertion is well known to proceed efficiently into secondary and tertiary C–H bonds. A. Srikrishna of the Indian Institute of Science, Bangalore found (Synlett 2011, 2343) that insertion into the methyl C–H of 22 also worked smoothly to deliver 23. The macrocyclic oligopeptide valinomycin 24 has nine isopropyl groups. It is remarkable, as observed (Org. Lett. 2011, 13, 5096) by Cosimo Annese of the Università di Bari and Paul G. Williard of Brown University, that direct oxidation of 24 with methyl(trifluoromethyl) dioxirane in acetone specifically hydroxylated at 8 (45.5%, our numbering), 7 (28.5%), and 6 (26%).

Advances in Organic Functional Group Transformation

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carboxylic Acids ◽  
Allyl Ether ◽  
Primary Alcohols ◽  
Ru Catalyst ◽  
University Of Technology ◽  
National University ◽  
Tokyo Institute ◽  
Institute Of Technology ◽  
The University ◽  
Technological University

There have been several significant advances in N-alkylation using alcohols. Matthias Beller of Universität Rostock devised (Angew. Chem. Int. Ed. 2010, 49, 8126) a Ru catalyst for the amination of secondary and benzylic primary alcohols with ammonia. Dieter Vogt of the Eindhoven University of Technology reported (Angew. Chem. Int. Ed. 2010, 49, 8130) related transformations. Pei-Qiang Huang of Xiamen University showed (Chem. Commun. 2010, 46, 7834) that debenzylation of 3 in methanol led to the N-methyl amine 4. Parallel results have been reported with Ir (J. Am. Chem. Soc. 2010, 132, 15108), Au (Chem. Eur. J. 2010, 16, 13965), and Cu (Chem. Lett. 2010, 39, 1182). Peter J. Scammells of Monash University found (J. Org. Chem. 2010, 75, 4806) that demethylation of an N-oxide could be effected with Fe powder. Yao Fu and Qingxiang Guo of the University of Science and Technology of China N-vinylated (Tet. Lett. 2010, 51, 5476) a sulfonamide 7 with vinyl acetate and a Pd catalyst. Acyl amides could also be N-vinylated under these conditions. Hirokazu Urabe of the Tokyo Institute of Technology reported (Org. Lett. 2010, 12, 4137) that the stereodefined secondary sulfonamide of 9 could be displaced by an internal nucleophile, to give the product 11 with inversion of absolute configuration. Teruo Umemoto of IM&T Research devised (J. Am. Chem. Soc. 2010, 132, 18199) the remarkable fluorinating agent 13. In addition to converting secondary alcohols to the corresponding fluorides and ketones to gem-difluorides, 13 cleanly converted the carboxylic acids of 12 to trifluoromethyl groups. Paul G. Williard of Brown University demonstrated (Org. Lett. 2010, 12, 5378) that LDA converted an allyl ether 15 specifically to the (Z)-propenyl ether 16. Phil Lee Ho of Kangwon National University and Sunggak Kim of Nanyang Technological University could add (Angew. Chem. Int. Ed. 2010, 49, 6806) a phosphate to an alkyne 17 to make either the less substituted or the more substituted enol phosphate. Professor Kim reported (J. Org. Chem. 2010, 75, 7928) similar results with the addition of carboxylic acids.

Best Synthetic Methods: Oxidation and Reduction

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Butyl Alcohol ◽  
Hydrogen Gas ◽  
Synthetic Methods ◽  
Pt Catalyst ◽  
Ru Catalyst ◽  
Methyl Levulinate ◽  
Benzyl Ethers ◽  
Marked Preference ◽  
Institute Of Technology ◽  
The University

Although methods both for reduction and for oxidation are well developed, there is always room for improvement. While ketones are usually reduced using metal hydrides, hydrogen gas is much less expensive on scale. Charles P. Casey of the University of Wisconsin has devised (J. Am. Chem. Soc. 2007, 129, 5816) an Fe-based catalyst that effects the transformation of 1 to 2. Note that the usually very reactive monosubstituted alkene is not reduced and does not migrate. Takeshi Oriyama of Ibaraki University has developed a catalyst, also Fe-based (Chemistry Lett. 2007, 38) for reducing aldehydes to ethers. Using this approach, an alcohol such as 3 can be converted into a variety of substituted benzyl ethers, including 5. Simple aliphatic aldehydes and alcohols also work well. Oxidation of alcohols to aldehydes or ketones is one of the most common of organic transformations. Several new processes catalytic in metal have been put forward. Tharmalingam Punniyamurthy of the Indian Institute of Technology, Guwahati has found (Adv. Synth. Cat. 2007, 349, 846) that catalytic V(IV) oxide on silica gel, stirred with t-butyl hydroperoxide in t-butyl alcohol at room temperature smoothly oxidized 6 to 7. After the reaction, the catalyst was separated by filtration. Another carbonyl can also serve as the hydride acceptor, but then the transfer can be reversible. Jonathan M. J. Williams of the University of Bath has shown (Tetrahedron Lett. 2007, 48, 3639) that with a Ru catalyst, methyl levulinate 9 could serve as the hydride acceptor, with the byproduct alcohol being drained off as the lactone 11. Hansjörg Grützmacher of the ETH Zürich developed an Ir catalyst (Angew. Chem. Int. Ed. 2007, 46, 3567) with benzoquinone as the net oxidant. that showed marked preference for the oxidation of primary over secondary alcohols. Yasuhiro Uozumi of the Institute for Molecular Science, Aichi, has devised (Angew. Chem. Int. Ed . 2007, 46, 704) a nanoencapsulated Pt catalyst that worked well with O2 or even with air. The catalyst was easily separated from the product, and maintained its activity over several cycles.

Functionalization and Homologation of C-H Bonds

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Crop Protection ◽  
Oxidative Cyclization ◽  
South Florida ◽  
State University ◽  
Ru Catalyst ◽  
University Of Oklahoma ◽  
Princeton University ◽  
La Jolla ◽  
The University ◽  
Technological University

Justin Du Bois of Stanford University developed (J. Am. Chem. Soc. 2010, 132, 10202) a Ru catalyst for the stereoretentive hydroxylation of 1 to 2. John T. Groves of Princeton University effected (J. Am. Chem. Soc. 2010, 132, 12847) equatorial chlorination of the test substrate 3. Kenneth M. Nicholas of the University of Oklahoma found (J. Org. Chem. 2010, 75, 7644) that I2 catalyzed the amination of 5. Thorsten Bach of the Technische Universität München established (Org. Lett. 2010, 12, 3690) that the amination of 7 proceeded with significant diastereoselectivity. Phil S. Baran of Scripps/La Jolla compiled (Synlett 2010, 1733) an overview of the development of C-H oxidation. Tethering can improve the selectivity of C-H functionalization. X. Peter Zhang of the University of South Florida devised (Angew. Chem. Int. Ed. 2010, 49, 10192) a Co catalyst for the cyclization of 9 to 10. Teck-Peng Loh of Nanyang Technological University established (Angew. Chem. Int. Ed. 2010, 49, 8417) conditions for the oxidation of 11 to 12. Jin-Quan Yu, also of Scripps/La Jolla, effected (J. Am. Chem. Soc. 2010, 132, 17378) carbonylation of methyl C-H of 13 to give 14. Sunggak Kim, now also at Nanyang Technological University, established (Synlett 2010, 1647) conditions for the free-radical homologation of 15 to 17. Gong Chen of Pennsylvania State University extended (Org. Lett. 2010, 12, 3414) his work on remote Pd-mediated activation by cyclizing 18 to 19. Many schemes have been developed in recent years for the oxidation of substrates to reactive electrophiles. Gonghua Song of the East China University of Science and Technology and Chao-Jun Li of McGill University reported (Synlett 2010, 2002) Fe nanoparticles for the oxidative coupling of 20 with 21. Zhi-Zhen Huang of Nanjing University found (Org. Lett. 2010, 12, 5214) that protonated pyrrolidine 25 was important for mediating the site-selective coupling of 24 with 23. Y. Venkateswarlu of the Indian Institute of Chemical Technology, Hyderabad, was even able (Tetrahedron Lett. 2010, 51, 4898) to effect coupling with a cyclic alkene 28. AB3217-A 32, isolated in 1992, was shown to have marked activity against two spotted spider mites. Christopher R. A. Godfrey of Syngenta Crop Protection, Münchwilen, prepared (Synlett 2010, 2721) 32 from commercial anisomycin 30a. The key step in the synthesis was the oxidative cyclization of 30b to 31.

Functional Group Oxidation and Reduction

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Direct Conversion ◽  
University Of Mississippi ◽  
Ru Catalyst ◽  
Mo Catalyst ◽  
University Of Arizona ◽  
Institute Of Technology ◽  
Diastereoselective Reduction ◽  
The University ◽  
University Of Manchester ◽  
Mediated Reduction

Debabrata Maiti of the Indian Institute of Technology Bombay found (Chem. Commun. 2012, 48, 4253) that the relatively inexpensive Pd(OAc)2 effectively catalyzed the decarbonylation of an aldehyde 1 to the hydrocarbon 2. Hui Lou of Zhejiang University used (Adv. Synth. Catal. 2011, 353, 2577) a Mo catalyst to effect reduction of the ester 3 to the hydrocarbon 4, with retention of all the skeletal carbons. Jon T. Njardarson of the University of Arizona showed (Chem. Commun. 2012, 48, 7844) that the allylic ether 5 could be reduced with high regioselectivity to give 6. José Barluenga and Carlos Valdés of the Universidad de Oviedo effected (Angew. Chem. Int. Ed. 2012, 51, 5950) the direct conversion of a ketone 7 to the azide 8. Although no cyclic ketones were included in the examples, there is a good chance that this will be the long-sought diastereoselective reduction of a cyclohexanone to the equatorial amine. Hideo Nagashima of Kyushu University reduced (Chem. Lett. 2012, 41, 229) the acid 9 directly to the aldehyde 1 using a ruthenium catalyst with the bis silane 10. Georgii I. Nikonov of Brock University described (Adv. Synth. Catal. 2012, 354, 607) a similar Ru-mediated silane reduction of an acid chloride to the aldehyde. Professor Nagashima used (Angew. Chem. Int. Ed. 2012, 51, 5363) his same Ru catalyst to reduce the ester 11 to the protected amine 12. Shmaryahu Hoz of Bar-Ilan University used (J. Org. Chem. 2012, 77, 4029) photostimulation to promote the SmI2-mediated reduction of a nitrile 13 to the amine 14. Bakthan Singaram of the University of California, Santa Cruz effected (J. Org. Chem. 2012, 77, 221) the same transformation with InCl3/NaBH4. David J. Procter of the University of Manchester described (J. Org. Chem. 2012, 77, 3049) what promises to be a general method for activating Sm metal to form SmI2. Mark T. Hamann of the University of Mississippi directly reduced (J. Org. Chem. 2012, 77, 4578) the nitro group of 15 to the alkylated amine 16. Cleanly oxidizing aromatic methyl groups to the level of the aldehyde without overoxidation has been a challenge.

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.

Metal-Mediated C–C Ring Construction: The Carreira Synthesis of (+)-Asperolide C

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Ring Expansion ◽  
Ethyl Acrylate ◽  
Heck Cyclization ◽  
University Of Oxford ◽  
Silyl Enol Ether ◽  
Emory University ◽  
Institute Of Technology ◽  
The University ◽  
Technological University

Djamaladdin G. Musaev and Huw M. L. Davies of Emory University effected (Chem. Sci. 2013, 4, 2844) enantioselective cyclopropanation of ethyl acrylate 2 with the α-diazo ester 1 to give 3 in high ee. Philippe Compain of the Université de Strasbourg used (J. Org. Chem. 2013, 78, 6751) SmI2 to cyclize 4 to the cyclobutanol 5. Jianrong (Steve) Zhou of Nanyang Technological University effected (Chem. Commun. 2013, 49, 11758) enantioselective Heck addition of 7 to the prochiral ester 6 to give the cyclopentene 8. Liu-Zhu Gong of USTC, Hefei added (Org. Lett. 2013, 15, 3958) the Rh enolate from the enantioselective ring expansion of the α-diazo ester 9 to the nitroalkene 10, to give 11 in high de. Stephen P. Fletcher of the University of Oxford set (Angew. Chem. Int. Ed. 2013, 52, 7995) the cyclic quaternary center of 14 by the enantioselective conjugate addition to 12 of the alkyl zirconocene derived from 13. Alexandre Alexakis of the University of Geneva reported (Chem. Eur. J. 2013, 19, 15226) high ee from the conjugate addition of alkenyl Al reagents (not illustrated) to 12. Paultheo von Zezschwitz of Philipps-Universität Marburg prepared (Adv. Synth. Catal. 2013, 355, 2651) the silyl enol ether 17 by trapping the intermediate from the conjugate addition of 16 to 15. Stefan Bräse of the Karlsruhe Institute of Technology effected (Eur. J. Org. Chem. 2013, 7110) conjugate addition to the prochiral dienone 18 to give the highly substi­tuted cyclohexenone 19. Ping Tian and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry cyclized (J. Am. Chem. Soc. 2013, 135, 11700) 20 to the kinetic, less stable epimer of the diketone 21. Rh-mediated intramolecular C–H insertion has been a powerful tool for the con­struction of cyclopentane derivatives. Douglass F. Taber of the University of Delaware found (J. Org. Chem. 2013, 78, 9772) that the Rh carbene derived from 22 was dis­criminating enough to target the more nucleophilic C–H bond, leading to the cyclohexanone 23. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 3666) high diastereoselectivity in the intramolecular Heck cyclization of 24 to 25.

scholarly journals Opening statement

IDEA JOURNAL ◽  
1969 ◽  
pp. 4-5
Author(s):  
Marina Lommerse
Keyword(s):  
Interior Design ◽  
South Australia ◽  
Architecture Education ◽  
Interior Architecture ◽  
Inaugural Meeting ◽  
South Wales ◽  
University Of Technology ◽  
Royal Melbourne Institute ◽  
Institute Of Technology ◽  
The University

Interested Australian universities with Interior Design/Interior Architecture degrees held an inaugural meeting in Sydney in 1996 to elicit interest in an association to advocate Interior Design/Interior Architecture education and research. In 1997 IDEA was formalised to encourage and support excellence in the discipline. This is the Inaugural publication of the annual ‘IDEA Referred Design Scheme’, one of the activities the IDEA committee promotes. Participating universities include: Curtin University of Technology, Queensland College of Art, Queensland University of Technology, Northern Territory University, Royal Melbourne Institute of Technology, Swinburne University of Technology, University of New South Wales, University of South Australia and the University of Technology Sydney.

Sign in / Sign up

Export Citation Format

Share Document