Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes

被引：46

作者：

Balaguer, Andrea-Nekane ^{[1
]}

Companyo, Xavier ^{[1
]}

Calvet, Teresa ^{[2
]}

Font-Bardia, Merce ^{[2
]}

Moyano, Albert ^{[1
]}

Rios, Ramon ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

[2] Univ Barcelona, Dept Cristal Log Mineral & Diposits, E-08028 Barcelona, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 02期

关键词：

Diastereoselective catalysis; Organocatalysis; Heterocycles; Michael addition; Nitrostyrenes; N; O-Aminals; DYNAMIC KINETIC RESOLUTION; ALPHA-AMINO-ACIDS; ASYMMETRIC ADDITION; ANIONS; CONSTRUCTION; AZLACTONES; PSYMBERIN; ACYLATION;

D O I：

10.1002/e.joc.200801005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and novel oxazol-5-one addition to nitrostyrenes is reported. The reaction is catalyzed by tertiary amines and yields the corresponding adducts with total regio- and diastereoselectivity. The addition exclusively takes place at the C-2 position of oxazol-5-ones, furnishing diastereopure N,O-aminals. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：199 / 203

页数：5

共 36 条

[1] [Anonymous], 1997, PROGRAM CRYSTAL STRU
[2] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts
Berkessel, A
Cleemann, F
Mukherjee, S
Müller, TN
Lex, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) : 807 - 811
[3] Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
Berkessel, A
Mukherjee, S
Cleemann, F
Müller, TN
Lex, J
[J]. CHEMICAL COMMUNICATIONS, 2005, (14) : 1898 - 1900
[4] Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
Berkessel, Albrecht
Mukherjee, Santanu
Mueller, Thomas N.
Cleemann, Felix
Roland, Katrin
Brandenburg, Marc
Neudoerfl, Joerg-M.
Lex, Johann
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) : 4319 - 4330
[5] Organocatalytic asymmetric synthesis of α,α-disubstituted α-amino acids and derivatives
Cabrera, Silvia
Reyes, Efraim
Aleman, Jose
Milelli, Andrea
Kobbelgaard, Sara
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) : 12031 - 12037
[6] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
Christoffers, J
Baro, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
[7] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[8] 2-V
[9] Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family
Cichewicz, RH
Valeriote, FA
Crews, P
[J]. ORGANIC LETTERS, 2004, 6 (12) : 1951 - 1954
[10] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

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