Unified Azoline and Azole Syntheses by Optimized Aza‐Wittig Chemistry
作者： Patrick Loos , Cyril Ronco , Matthias Riedrich , Hans-Dieter Arndt
关键词: Tosyl 、 Racemization 、 Wittig reaction 、 Chemistry 、 Amide 、 Stereochemistry 、 Ring (chemistry) 、 Thio- 、 Diazo 、 Thioester
摘要: Intramolecular aza-Wittig ring closures were applied to synthesize thiazolines, oxazolines, and imidazolines from β-azido thioester, ester, amide precursors. The cyclization precursors obtained amino acid derivatives. Optimized conditions for diazo transfer with a fast rate racemization suppression, (thio)esterification, coupling reactions are described. closure reaction can be executed PPh3 under neutral was found highly chemoselective five-membered rings. If groups activated tosyl groups, smooth intramolecular of iminophosphoranes furnished enantiopure imidazoline products position-specific protection. This aza-Wittig-based azoline synthesis then extended double furnish catenated building blocks common peptide natural product their analogues.
sci-hub.se 参考文章(97)
Yu.G. Gololobov, N.I. Gusar', M.P. Chaus, Reactions of trivalent phosphorus compounds with azides containing a mobile H-atom : A conception of phosphazo-compound spirocyclization mechanism Tetrahedron. ,vol. 41, pp. 793- 799 ,(1985) , 10.1016/S0040-4020(01)96459-2
David Tanner, Peter Somfai, From aziridines to carbapenems via a novel β-lactam ring closure : An enantioselective synthesis of (+)-PS-5 Tetrahedron. ,vol. 44, pp. 619- 624 ,(1988) , 10.1016/S0040-4020(01)85849-X
David R. Williams, Patrick D. Lowder, Yu-Gui Gu, Dawn A. Brooks, Studies of mild dehydrogenations in heterocyclic systems Tetrahedron Letters. ,vol. 38, pp. 331- 334 ,(1997) , 10.1016/S0040-4039(96)02344-1
Eric F. V. Scriven, Kenneth Turnbull, Azides: their preparation and synthetic uses Chemical Reviews. ,vol. 88, pp. 297- 368 ,(1988) , 10.1021/CR00084A001
Yomadis A. Ortiz Barbosa, David J. Hart, Nabi A. Magomedov, Spiroquinazoline support studies: methods for the preparation of imidazoloindolines from oxindoles Tetrahedron. ,vol. 62, pp. 8748- 8754 ,(2006) , 10.1016/J.TET.2006.06.103
Tuoping Luo, Stuart L. Schreiber, Gold(I)-catalyzed coupling reactions for the synthesis of diverse small molecules using the build/couple/pair strategy. Journal of the American Chemical Society. ,vol. 131, pp. 5667- 5674 ,(2009) , 10.1021/JA900414S
Wataru Kurosawa, Toshiyuki Kan, Tohru Fukuyama, Stereocontrolled total synthesis of (-)-ephedradine A (orantine). Journal of the American Chemical Society. ,vol. 125, pp. 8112- 8113 ,(2003) , 10.1021/JA036011K
Hisato Takeuchi, Shunichi Yanagida, Toru Ozaki, Satoshi Hagiwara, Shoji Eguchi, Synthesis of novel carbo- and heteropolycycles. 12. A new versatile synthesis of oxazoles by intramolecular aza-Wittig reaction Journal of Organic Chemistry. ,vol. 54, pp. 431- 434 ,(1989) , 10.1021/JO00263A033
M. Regitz, D. Stadler, H. Schwall, A. Liedhegener, H. J. Geelhaar, F. Menz, J. Hocker, J. Rüter, W. Anschütz, Neuere Methoden der präparativen organischen Chemie VI. Diazogruppen‐Übertragung Angewandte Chemie. ,vol. 79, pp. 786- 801 ,(1967) , 10.1002/ANGE.19670791707
Paul T. Nyffeler, Chang-Hsing Liang, Kathryn M. Koeller, Chi-Huey Wong, The chemistry of amine-azide interconversion: catalytic diazotransfer and regioselective azide reduction. Journal of the American Chemical Society. ,vol. 124, pp. 10773- 10778 ,(2002) , 10.1021/JA0264605