Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst

被引：20

作者：

Lygo, Barry ^{[1
]}

Davison, Christopher ^{[1
]}

Evans, Timothy ^{[1
]}

Gilks, James A. R. ^{[1
]}

Leonard, John ^{[2
]}

Roy, Claude-Eric ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England

来源：

TETRAHEDRON | 2011年 / 67卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

Asymmetric catalysis; Aldol; Organocatalysis; Diamine; Stereoselective; ASYMMETRIC DIRECT ALDOL; PHASE-TRANSFER CATALYSIS; GLYCINE IMINES; MICHAEL ADDITION; PROLINE; WATER; CYCLOHEXANONE; ALKYLATION; ALDEHYDES; EFFICIENT;

D O I：

10.1016/j.tet.2011.09.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four-step synthesis of a chiral primary tertiary diamine salt, possessing a tropos dibenz[c,e]azepine ring is described. It is shown that 3.5-5 mol % of this salt is capable of promoting highly enantioselective crossed-aldol reactions between cyclohexanone and a series of aromatic aldehydes. In all cases, the aldol reactions proceed with high diastereoselectivity for the anti-aldol product. The outcome of crossed-aldol reactions involving other cyclic ketones and acyclic ketones are also described. All examples involving cyclic ketones result in selectivity for the anti-aldol products, whereas acyclic ketones were found to favour the syn-aldol products. A discussion on the role of the chiral primary tertiary diamine salt in the catalysis of the aldol reactions is also presented. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：10164 / 10170

页数：7

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