Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine

被引：100

作者：

Chen, Wen-Bing ^{[1
,2
]}

Du, Xi-Lin ^{[3
]}

Cun, Lin-Feng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

[3] Fourth Mil Med Univ, Tangdu Hosp, Dept Gen Surg, Xian 710038, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Aldol reaction; Acetaldehyde; Asymmetric catalysis; Isatins; CONVOLUTAMYDINE-A; MANNICH REACTIONS; 2-STEP SYNTHESIS; ALKALOIDS; PROLINE; ORGANOCATALYST; CONDENSATION; DERIVATIVES; TMC-95A; KETONES;

D O I：

10.1016/j.tet.2009.12.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective aldol reaction of acetaldehyde and a wide scope of isatins has been presented only using readily available 4-hydroxydiarylprolinol as catalyst, affording various desired 3-substituted 3-hydroxyindolin-2-one adducts with moderate to high yield (up to 95%) and good enantioselectivities (up to 98% ee). This method not only represents an example of concise stereoselective synthesis of enantiopure (R)-convolutamydines B and E, but also firstly exhibits expedient asymmetric synthesis optically active (-)-donaxaridine and (R)-chimonamidine. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1441 / 1446

页数：6