Organocatalyzed C–C Ring Construction: The Jørgenson Synthesis of (+)-Estrone

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
New England ◽  
Hydroxy Ketone ◽  
Ethyl Vinyl Ether ◽  
State University ◽  
Ethyl Vinyl ◽  
National University ◽  
North Dakota State University ◽  
Indian Institute Of Science ◽  
The University ◽  
Pais Vasco

Ana Maria Faísca Phillips and Maria Teresa Barros of the Universidade Nova de Lisboa added (Eur. J. Org. Chem. 2014, 152) the bromo ester 1 to cinnamaldehyde 2 to give the cyclopropyl phosphonate 3 in high ee. Mukund P. Sibi and Jayaraman Sivaguru of North Dakota State University used (Angew. Chem. Int. Ed. 2014, 53, 5604) an organocatalyst to mediate the 2+2 photocycloaddition of 4, leading to 5. Shu-Li You of the Shanghai Institute of Organic Chemistry expanded (Org. Lett. 2014, 16, 1810) the four-membered ring of 6 to create the cyclopentanone 7 in high ee. Damien Bonne and Jean Rodriguez of Aix-Marseille Université condensed (Chem. Eur. J. 2014, 20, 410) the cyclopentanone 8 with 9 to give 10. Santanu Mukherjee of the Indian Institute of Science, Bangalore added (Chem. Sci. 2014, 5, 1627) the lac­tone 12 to the prochiral 11 to give 13 with remarkable diastereo- and enantiocontrol. Yixin Lu of the National University of Singapore constructed (Angew. Chem. Int. Ed. 2014, 53, 5643) the cyclopentene 16 by adding 14 to the allene 15. Efraim Reyes and Jose L. Vicario of the Universidad del País Vasco prepared (Chem. Eur. J. 2014, 20, 2145) the highly substituted cyclohexene 19 by combining 17 and 18. Maurizio Benaglia of the Università degli Studi di Milano added (Adv. Synth Catal. 2014, 356, 493) the ketone 20 to 21 to create the cyclohexanone 22. Ben W. Greatrex of the University of New England in Australia used (J. Org. Chem. 2014, 79, 5088) an organocatalyst to cyclize the symmetrical dialdehyde 23 to the α-hydroxy ketone 24. Dieter Enders of RWTH Aachen added (Org. Lett. 2014, 16, 2954) the β-keto ester 25 to 26 to give an intermediate that was further condensed with 27 to complete the preparation of 28. Eric N. Jacobsen of Harvard University prepared (Angew. Chem. Int. Ed. 2014, 53, 5912) the cycloheptenone 30 by the enantioselective intermolecular addition of the pyrylium salt derived from 29 to ethyl vinyl ether. Bor-Cherng Hong of the National Chung Cheng University initiated (Org. Lett. 2014, 16, 2724) the assembly of the steroid derivative 33 by the enantioselective addition of 32 to the unsaturated aldehyde 31.

Flow Chemistry

2015 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Continuous Flow ◽  
Flow Chemistry ◽  
Ethyl Vinyl Ether ◽  
University Of Michigan ◽  
Ethyl Vinyl ◽  
Photochemical Rearrangement ◽  
Osaka Prefecture ◽  
La Jolla ◽  
University Of Bristol ◽  
The University

Timothy F. Jamison at MIT developed (Org. Lett. 2013, 15, 710) a metal-free continuous-flow hydrogenation of alkene 1 using the protected hydroxylamine reagent 2 in the presence of free hydroxylamine. The reduction of nitroindole 4 to the corresponding aniline 5 using in situ-generated iron oxide nanocrystals in continuous flow was reported (Angew. Chem. Int. Ed. 2012, 51, 10190) by C. Oliver Kappe at the University of Graz. A flow method for the MPV reduction of ketone 6 to alcohol 7 was disclosed (Org. Lett. 2013, 15, 2278) by Steven V. Ley at the University of Cambridge. Corey R.J. Stephenson, now at the University of Michigan, developed (Chem. Commun. 2013, 49, 4352) a flow deoxygenation of alcohol 8 to yield 9 using visible light photoredox catalysis. Stephen L. Buchwald at MIT demonstrated (J. Am. Chem. Soc. 2012, 134, 12466) that arylated acetaldehyde 11 could be generated from aminopyridine 10 by diazonium formation and subsequent Meerwein arylation of ethyl vinyl ether in flow. The team of Takahide Fukuyama and Ilhyong Ryu at Osaka Prefecture University showed (Org. Lett. 2013, 15, 2794) that p-iodoanisole (12) could be converted to amide 13 via low-pressure carbonylation using carbon monoxide generated from mixing formic and sulfuric acids. The continuous-flow Sonogashira coupling of alkyne 14 to produce 15 using a Pd-Cu dual reactor was developed (Org. Lett. 2013, 15, 65) by Chi-Lik Ken Lee at Singapore Polytechnic. A tandem Sonogashira/cycloisomerization procedure to convert bromopyridine 16 to aminoindolizine 18 in flow was realized (Adv. Synth. Cat. 2012, 354, 2373) by Keith James at Scripps, La Jolla. A procedure for the Pauson-Khand reaction of alkene 19 to produce the bicycle 20 in a photochemical microreactor was reported (Org. Lett. 2013, 15, 2398) by Jun-ichi Yoshida at Kyoto University. Kevin I. Booker-Milburn at the University of Bristol discovered (Angew. Chem. Int. Ed. 2013, 52, 1499) that irradiation of N-butenylpyrrole 21 in flow produced the rearranged tricycle 22. Professor Jamison described (Angew. Chem. Int. Ed. 2013, 52, 4251) a unique peptide coupling involving the photochemical rearrangement of nitrone 23 to the hindered dipeptide 24 in continuous flow.

Organocatalyzed C–C Ring Construction: The Mihovilovic Synthesis of Piperenol B

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
State University ◽  
Air Oxidation ◽  
Microbial Oxidation ◽  
Max Planck ◽  
National Chemical Laboratory ◽  
Chemical Laboratory ◽  
Northwestern University ◽  
National University ◽  
The University ◽  
Oregon State University

M. Kevin Brown of Indiana University prepared (J. Am. Chem. Soc. 2015, 137, 3482) the cyclobutane 3 by the organocatalyzed addition of 2 to the alkene 1. Karl Anker Jørgensen of Aarhus University assembled (J. Am. Chem. Soc. 2015, 137, 1685) the complex cyclobutane 7 by the addition of 5 to the acceptor 4, followed by conden­sation with the phosphorane 6. Zhi Li of the National University of Singapore balanced (ACS Catal. 2015, 5, 51) three enzymes to effect enantioselective opening of the epoxide 8 followed by air oxidation to 9. Gang Zhao of the Shanghai Institute of Organic Chemistry and Zhong Li of the East China University of Science and Technology added (Org. Lett. 2015, 17, 688) 10 to 11 to give 12 in high ee. Akkattu T. Biju of the National Chemical Laboratory combined (Chem. Commun. 2015, 51, 9559) 13 with 14 to give the β-lactone 15. Paul Ha-Yeon Cheong of Oregon State University and Karl A. Scheidt of Northwestern University reported (Chem. Commun. 2015, 51, 2690) related results. Dieter Enders of RWTH Aachen University constructed (Chem. Eur. J. 2015, 21, 1004) the complex cyclopentane 20 by the controlled com­bination of 16, 17, and 18, followed by addition of the phosphorane 19. Derek R. Boyd and Paul J. Stevenson of Queen’s University Belfast showed (J. Org. Chem. 2015, 80, 3429) that the product from the microbial oxidation of 21 could be protected as the acetonide 22. Ignacio Carrera of the Universidad de la República described (Org. Lett. 2015, 17, 684) the related oxidation of benzyl azide (not illustrated). Manfred T. Reetz of the Max-Planck-Institut für Kohlenforschung and the Philipps-Universität Marburg found (Angew. Chem. Int. Ed. 2014, 53, 8659) that cytochrome P450 could oxidize the cyclohexane 23 to the cyclohexanol 24. F. Dean Toste of the University of California, Berkeley aminated (J. Am. Chem. Soc. 2015, 137, 3205) the ketone 25 with 26 to give 27. Benjamin List, also of the Max-Planck-Institut für Kohlenforschung, reported (Synlett 2015, 26, 1413) a parallel investigation. Philip Kraft of Givaudan Schweiz AG and Professor List added (Angew. Chem. Int. Ed. 2015, 54, 1960) 28 to 29 to give 30 in high ee.

C–N Ring Construction: The Waser Synthesis of Jerantinine E

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Ni Catalyst ◽  
University Of Alberta ◽  
Princeton University ◽  
In Situ Preparation ◽  
National University ◽  
The University ◽  
École Polytechnique ◽  
Pais Vasco ◽  
Multicomponent Coupling

James A. Bull of Imperial College London prepared (J. Org. Chem. 2013, 78, 6632) the aziridine 2 with high diastereocontrol by adding the anion of diiodomethane to the imine 1. Karl Anker Jørgensen of Aarhus University observed (Chem. Commun. 2013, 49, 6382) high ee in the distal aziridination of 3 to give 4. Benito Alcaide of the Universidad Complutense de Madrid and Pedro Almendros of ICOQ- CSIC Madrid reduced (Adv. Synth. Catal. 2013, 355, 2089) the β-lactam 5 to the azetidine 6. Hiroaki Sasai of Osaka University added (Org. Lett. 2013, 15, 4142) the allenoate 8 to the imine 7, delivering the azetidine 9 in high ee. Tamio Hayashi of Kyoto University, the National University of Singapore, and A*STAR devised (J. Am. Chem. Soc. 2013, 135, 10990) a Pd catalyst for the enanti­oselective addition of the areneboronic acid 11 to the pyrroline 10 to give 12. Ryan A. Brawn of Pfizer (Org. Lett. 2013, 15, 3424) reported related results. Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne developed (J. Am. Chem. Soc. 2013, 135, 11772) a Ni catalyst for the cyclization of the formamide 13 to the lactam 14. Andrew D. Smith of the University of St. Andrews used (Org. Lett. 2013, 15, 3472) an organocatalyst to cyclize 15 to 16. Jose L. Vicario of the Universidad del Pais Vasco effected (Synthesis 2013, 45, 2669) the multicomponent coupling of 17, 18, and 19, mediated by an organocatalyst, to construct 20 in high ee. André Beauchemin of the University of Ottawa explored (J. Org. Chem. 2013, 78, 12735) the thermal cyclization of ω-alkenyl hydroxyl amines such as 21. Abigail G. Doyle of Princeton University developed (Angew. Chem. Int. Ed. 2013, 52, 9153) a Ni catalyst for the enantioselective addition of aryl zinc bromides such as 24 to the pro­chiral 23, to give 25 in high ee. Dennis G. Hall of the University of Alberta developed (Angew. Chem. Int. Ed. 2013, 52, 8069) an in situ preparation of the allyl boronate 26 in high ee. Addition to the aldehyde 27 proceeded with high diasteroselectivity.

C–O Ring Formation

2017 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Science And Technology ◽  
State University ◽  
University Of Michigan ◽  
Colorado State University ◽  
Boston University ◽  
Chapel Hill ◽  
Chiral Phosphoric Acid ◽  
National University ◽  
University Of Bristol ◽  
The University

The enantioselective bromocyclization of dicarbonyl 1 to form dihydrofuran 3 using thiocarbamate catalyst 2 was developed (Angew. Chem. Int. Ed. 2013, 52, 8597) by Ying-Yeung Yeung at the National University of Singapore. Access to dihydrofuran 5 from the cyclic boronic acid 4 and salicylaldehyde via a morpholine-mediated Petasis borono-Mannich reaction was reported (Org. Lett. 2013, 15, 5944) by Xian-Jin Yang at East China University of Science and Technology and Jun Yang at the Shanghai Institute of Organic Chemistry. Chiral phosphoric acid 7 was shown (Angew. Chem. Int. Ed. 2013, 52, 13593) by Jianwei Sun at the Hong Kong University of Science and Technology to catalyze the enantioselective acetalization of diol 6 to form tetrahydrofuran 8 with high stereoselectivity. Jan Deska at the University of Cologne reported (Org. Lett. 2013, 15, 5998) the conversion of glutarate ether 9 to enantiopure tetrahy­drofuranone 10 by way of an enzymatic desymmetrization/oxonium ylide rearrange­ment sequence. Perali Ramu Sridhar at the University of Hyderabad demonstrated (Org. Lett. 2013, 15, 4474) the ring-contraction of spirocyclopropane tetrahydropyran 11 to produce tetrahydrofuran 12. Michael A. Kerr at the University of Western Ontario reported (Org. Lett. 2013, 15, 4838) that cyclopropane hemimalonate 13 underwent conver­sion to vinylbutanolide 14 in the presence of LiCl and Me₃N•HCl under microwave irradiation. Eric M. Ferreira at Colorado State University developed (J. Am. Chem. Soc. 2013, 135, 17266) the platinum-catalyzed bisheterocyclization of alkyne diol 15 to fur­nish the bisheterocycle 16. Chiral sulfur ylides such as 17, which can be synthesized easily and cheaply, were shown (J. Am. Chem. Soc. 2013, 135, 11951) by Eoghan M. McGarrigle at the University of Bristol and University College Dublin and Varinder K. Aggarwal at the University of Bristol to stereoselectively epoxidize a variety of alde­hydes, as exemplified by 18. The amine 20-catalyzed tandem heteroconjugate addition/Michael reaction of quinol 19 and cinnamaldehyde to produce bicycle 21 with very high ee was reported (Chem. Sci. 2013, 4, 2828) by Jeffrey S. Johnson at the University of North Carolina, Chapel Hill. Quinol ether 22 underwent facile photorearrangement–cycloaddition to 23 under irradiation, as reported (J. Am. Chem. Soc. 2013, 135, 17978) by John A. Porco, Jr. at Boston University and Corey R. J. Stephenson, now at the University of Michigan.

Aborigine and settler: archaeological air photography

Antiquity ◽  
1978 ◽  
Vol 52 (205) ◽  
pp. 95-99 ◽  
Author(s):  
Graham Connah
Keyword(s):  
New England ◽  
Aerial Photography ◽  
New South ◽  
Aerial Photographs ◽  
Archaeological Sites ◽  
Low Level ◽  
South Wales ◽  
National University ◽  
Great Tradition ◽  
The University

Australian students of archaeology could be excused for thinking that aerial photography is a technique with little archaeological application in their own country. Archaeological text books usually draw their examples of the uses of aerial photography from Europe or the Americas; even the pages of Antiquity, graced for many years by the work of J. K. St Joseph and others, suggest a similar geographic limitation. It is also a fact that there are not many published aerial photographs of Australian archaeological sites. In particular, the great tradition of low-level oblique photography with hand-held camera seems to have had comparatively little impact on Australian archaeology. There have been notable exceptions: for instance Bill Webster, of the University of New England, has taken low-level oblique infra red photographs of the Moore Creek Axe Quarry near Tamworth, New South Wales (Binns and Mc- Bryde, 1972; McBryde, 1974); Jim Bowler of the Australian National University provided photography of Lake Mungo (Mulvaney, 1975, P1.47), and Judy Birmingham of Sydney University has published an aerial photograph of the Irrawang Pottery (Birmingham, 1976)

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.

scholarly journals Reviewer Acknowledgements

2018 ◽  
Vol 6 (11) ◽  
pp. 271
Author(s):  
Robert Smith
Keyword(s):  
Hong Kong ◽  
Education And Training ◽  
The Philippines ◽  
Economic Research ◽  
State University ◽  
University Of Pittsburgh ◽  
National University ◽  
The University ◽  
And Training

Journal of Education and Training Studies (JETS) would like to acknowledge the following reviewers for their assistance with peer review of manuscripts for this issue. Many authors, regardless of whether JETS publishes their work, appreciate the helpful feedback provided by the reviewers. Their comments and suggestions were of great help to the authors in improving the quality of their papers. Each of the reviewers listed below returned at least one review for this issue.Reviewers for Volume 6, Number 11Adalberto Felipe Martinez, Federal University of São Carlos, BrazilAngel H. Y. Lai, Hong Kong Baptist University, Hong KongBenmarrakchi Fatimaezzahra, Chouaib Doukkali University, MoroccoBrenda L. Shook, National University, USACagla Atmaca, Pamukkale University, TurkeyChosang Tendhar, Long Island University (LIU), USACynthia M. Compton, Wingate University, USAEnisa Mede,Bahcesehir University,TurkeyErica D. Shifflet-Chila, Michigan State University, USAFroilan D. Mobo, Philippine Merchant Marine Academy, PhilippineHelena Reis, Polytechnic Institute of Leiria, PortugalHyesoo Yoo, Virginia Tech., USAIntakhab Khan, King Abdulaziz University, Saudi ArabiaJohn Bosco Azigwe, Bolgatanga Polytechnic, GhanaJohn Cowan, Edinburgh Napier University, UKJon S. Turner, Missouri State University, USAJonathan Chitiyo, University of Pittsburgh Bradford, USALorna T. Enerva, Polytechnic University of the Philippines, PhilippinesMan-fung Lo, The Hong Kong Polytechnic University, Hong KongMarcie Zaharee, The MITRE Corporation, USAMaurizio Sajeva, Pellervo Economic Research PTT, FinlandMehmet Inan, Marmara University, TurkeyMin Gui, Wuhan University, ChinaNicole Celestine, The University of Western Australia, AustraliaSadia Batool, Preston University Islamabad, PakistanSamad Mirza Suzani, Islamic Azad University, IranSandro Sehic, Oneida BOCES, USASelloane Pitikoe, University of Kwazulu-Natal, South AfricaSenem Seda Şahenk Erkan, Marmara University, TurkeyShu-wen Lin, Sojo University, JapanStamatis Papadakis, University of Crete, GreeceThomas K. F. Chiu, The University of Hong Kong, Hong KongRobert SmithEditorial AssistantOn behalf of,The Editorial Board of Journal of Education and Training StudiesRedfame Publishing9450 SW Gemini Dr. #99416Beaverton, OR 97008, USAURL: http://jets.redfame.com

scholarly journals Reviewer Acknowledgements

2017 ◽  
Vol 6 (1) ◽  
pp. 169
Author(s):  
Robert Smith
Keyword(s):  
Education And Training ◽  
Economic Research ◽  
Michigan State University ◽  
State University ◽  
American University ◽  
Kwazulu Natal ◽  
National University ◽  
The University ◽  
And Training

Journal of Education and Training Studies (JETS) would like to acknowledge the following reviewers for their assistance with peer review of manuscripts for this issue. Many authors, regardless of whether JETS publishes their work, appreciate the helpful feedback provided by the reviewers. Their comments and suggestions were of great help to the authors in improving the quality of their papers. Each of the reviewers listed below returned at least one review for this issue.Reviewers for Volume 6, Number 1Brenda L. Shook, National University, USACagla Atmaca, Pamukkale University, TurkeyCarole Fern Todhunter, The University of Nottingham, UKCharlotte Alverson, University of Oregon, USAChosang Tendhar, Long Island University (LIU), USAEnisa Mede, Bahcesehir University, TurkeyErica D. Shifflet-Chila, Michigan State University, USAGreg Rickwood, Nipissing University, CanadaHyesoo Yoo, Virginia Tech., USAIoannis Syrmpas, University of Thessaly, GreeceJohn Cowan, Edinburgh Napier University, UKLinda J. Rappel, Yorkville University/University of Calgary, CanadaMan-fung Lo, The Hong Kong Polytechnic University, Hong KongMassimiliano Barattucci, Ecampus University, ItalyMaurizio Sajeva, Pellervo Economic Research PTT, FinlandMehmet Inan, Marmara University, TurkeyMichail Kalogiannakis, University of Crete, GreeceMin Gui, Wuhan University, ChinaNerina Fernanda Sarthou, Universidad Nacional del Centro de la Provincia de Buenos Aires, ArgentinaPirkko Siklander, University of Lapland, FinlandRichard H. Martin, Mercer University, USARichard Penny, University of Washington Bothell, USARiyadh Tariq Kadhim Al-Ameedi, Babylon University, IraqRufaidah Kamal Abdulmajeed, Baghdad University, IraqSadia Batool, Preston University Islamabad, PakistanSelloane Pitikoe, University of Kwazulu-Natal, South AfricaSenem Seda Şahenk Erkan, Marmara University, TurkeySeyyedeh Mina Hamedi, Ferdowsi University of Mashhad, IranSisi Chen, American University of Health Sciences, USATilanka Chandrasekera, Oklahoma State University, USAYalçın Dilekli, Aksaray University, TurkeyYerlan Seisenbekov, Kazakh National Pedagogical University, KazakhstanYi Lu, American Institute for Research, USAYuChun Chen, Louisiana Tech University, USARobert SmithEditorial AssistantOn behalf of,The Editorial Board of Journal of Education and Training StudiesRedfame Publishing9450 SW Gemini Dr. #99416Beaverton, OR 97008, USAURL: http://jets.redfame.com

scholarly journals The Death of the Desk Crit

2019 ◽  
Author(s):  
Malini Srivastava ◽  
◽  
John Barton ◽  
Mike Christenson ◽  
◽  
...  
Keyword(s):  
Design Process ◽  
Stanford University ◽  
State University ◽  
University Of Minnesota ◽  
Teaching Models ◽  
Collaborative Capacity ◽  
Typical Day ◽  
North Dakota State University ◽  
The University ◽  
Movement Change

This paper describes three alternative architectural studio teaching models taught by the authors at the University of Minnesota and at Stanford University. The three models attempt to build independent and collaborative capacity in students and to emphasize iterative components of the design process. Collectively, the models reflect the authors’ shared conviction that studio education is quite pliable and available to a wide variety of changes in approach and methods.The three models discussed in this paper are the Harkness model, the Exchanges in the Thick Middle and Shifting Allegiances. The Harkness model was implemented and tested in early undergraduate studios at Stanford University. Exchanges in the Thick Middle and the Shifting Allegiances studios, studio pedagogy based in play frameworks of “movement, change, alternation, succession, association and separations” (Srivastava and Christenson 2018), have been tested at the University of Minnesota and North Dakota State University in both undergraduate and graduate studios. All three models are briefly introduced in this paper, followed by a description of the typical day and a typical review in the studios. The conclusions section briefly outlines the overlaps and differences in the three models.

Heteroaromatic Synthesis: The Tokuyama Synthesis of (−)-Rhazinilam

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Ni Catalyst ◽  
State University ◽  
Colorado State University ◽  
Ru Catalyst ◽  
Opioid Ligands ◽  
University Of Wisconsin ◽  
Rh Catalyst ◽  
Indian Institute Of Science ◽  
The University ◽  
École Polytechnique

Mei-Huey Lin of the National Changhua University of Education rearranged (J. Org. Chem. 2014, 79, 2751) the initial allene derived from 1 to the γ-chloroenone. Displacement with acetate followed by hydrolysis led to the furan 2. A. Stephen K. Hashmi of Ruprecht-Karls-Universität Heidelberg showed (Angew. Chem. Int. Ed. 2014, 53, 3715) that the Au-catalyzed conversion of the bis alkyne 3, mediated by 4, proceeded selectively to give 5. Tehshik P. Yoon of the University of Wisconsin used (Angew. Chem. Int. Ed. 2014, 53, 793) visible light with a Ru catalyst to rearrange the azide 6 to the pyrrole 7. Cheol-Min Park, now at UNIST, found (Chem. Sci. 2014, 5, 2347) that a Ni catalyst reorganized the methoxime 8 to the pyrrole 9. A Rh catalyst converted 8 to the corresponding pyridine (not illustrated). In the course of a synthesis of opioid ligands, Kenner C. Rice of the National Institute on Drug Abuse optimized (J. Org. Chem. 2014, 79, 5007) the preparation of the pyridine 11 from the alcohol 10. Vincent Tognetti and Cyrille Sabot of the University of Rouen heated (J. Org. Chem. 2014, 79, 1303) 12 and 13 under micro­wave irradiation to give the 3-hydroxy pyridine 14. Tomislav Rovis of Colorado State University prepared (J. Am. Chem. Soc. 2014, 136, 2735) the pyridine 17 by the Rh-catalyzed combination of 15 with 16. Fabien Gagosz of the Ecole Polytechnique rearranged (Angew. Chem. Int. Ed. 2014, 53, 4959) the azirine 18, readily available from the oxime of the β-keto ester, to the pyridine 19. Matthias Beller of the Universität Rostock used (Chem. Eur. J. 2014, 20, 1818) a Zn catalyst to mediate the opening of the epoxide 21 with the aniline 20. A Rh cata­lyst effected the oxidation and cyclization of the product amino alcohol to the indole 22. Sreenivas Katukojvala of the Indian Institute of Science Education & Research showed (Angew. Chem. Int. Ed. 2014, 53, 4076) that the diazo ketone 23 could be used to anneal a benzene ring onto the pyrrole 24, leading to the 2,7-disubstituted indole 25.

Sign in / Sign up

Export Citation Format

Share Document