Thiophosphoramide catalyzed asymmetric Michael addition of acetone to ftmctionalized nitrostyrenes: a convenient approach to optically active tetrahydropyrans

被引：22

作者：

Wu, Yang ^{[1
]}

Lu, Aidang ^{[1
]}

Liu, Yunfeng ^{[1
]}

Yu, Xiaolei ^{[1
]}

Wang, Youming ^{[1
]}

Wu, Guiping ^{[1
]}

Song, Haibin ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; HYDROGEN-BONDING DONORS; BETA-KETOESTERS; NITROOLEFINS; THIOUREA; AMINE; ORGANOCATALYSTS; EFFICIENT; ALDEHYDES; KETONES;

D O I：

10.1016/j.tetasy.2010.11.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Thiophosphoramide 5d was found to be an effective organocatalyst for the enantioselective Michael reaction of problematic acetone to various hydroxymethyl nitrostyrenes, affording the multisubstituted tetrahydropyrans with three stereogenic centers. The Michael addition products generated were obtained as a single diastereomer with enantioselectivities ranging from 46% to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2988 / 2992

页数：5

共 65 条

[1] Organocatalytic Enantioselective Olefin Aminofluorination [J].

Appayee, Chandrakumar ;

Brenner-Moyer, Stacey E. .

ORGANIC LETTERS, 2010, 12 (15) :3356-3359

[2]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[3] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins [J].

Cao, Chun-Li ;

Ye, Meng-Chun ;

Sun, Xiu-Li ;

Tang, Yong .

ORGANIC LETTERS, 2006, 8 (14) :2901-2904

[4] Enantiopure cycloalkane fused tetrahydropyrans through domino Michael-ketalizations with organocatalysis [J].

Chandrasekhar, Srivari ;

Mallikarjun, Kundarapu ;

Pavankumarreddy, Gangireddy ;

Rao, Kakita Veeramohana ;

Jagadeesh, Bharatam .

CHEMICAL COMMUNICATIONS, 2009, (33) :4985-4987

[5] Convenient transformation of optically active nitroalkanes into chiral aldoximes and nitriles [J].

Czekelius, C ;

Carreira, EM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :612-615

[6]

DIEGO D, 2009, J ORG CHEM, V74, P6163

[7] Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins [J].

Ding, Miao ;

Zhou, Feng ;

Qian, Zi-Qing ;

Zhou, Jian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) :2912-2914

[8] Organocatalytic asymmetric Michael addition of α-aryl cyclopentanones to nitroolefins for construction of adjacent quaternary and tertiary stereocenters [J].

Dong, Xiu-Qin ;

Teng, Huai-Long ;

Tong, Min-Chao ;

Huang, He ;

Tao, Hai-Yan ;

Wang, Chun-Jiang .

CHEMICAL COMMUNICATIONS, 2010, 46 (36) :6840-6842

[9] Enantioselective nitro-Michael reactions catalyzed by short peptides on water [J].

Freund, Matthias ;

Schenker, Sebastian ;

Tsogoeva, Svetlana B. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) :4279-4284

[10] Sugar-derived bifunctional thiourea organocatalyzed asymmetric Michael addition of acetylacetone to nitroolefins [J].

Gao, Peng ;

Wang, Chungui ;

Wu, Yang ;

Zhou, Zhenghong ;

Tang, Chuchi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (27) :4563-4566

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