Diastereoselective and enantioselective Henry (nitroaldol) reaction utilizing a guanidine-thiourea bifunctional organocatalyst

被引：162

作者：

Sohtome, Yoshihiro ^{[1
]}

Hashimoto, Yuichi

Nagasawa, Kazuo

机构：

[1] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan

[2] Tokyo Univ Agr & Technol, Dept Biotechnol & Life Sci, Fac Technol, Koganei, Tokyo 1848588, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 13期

关键词：

organocatalysis; bifunctional catalyst; guanidine; thiourea; Henry reaction;

D O I：

10.1002/ejoc.200600307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantio- and diastereoselective Henry reaction of various aldehydes with nitroethane was developed using the guanidine-thiourea bifunctional catalyst 1 (syn selectivity of 86:14 to 99:1 with 84-99 % ee). A variety of nitroalkanes was treated with unbranched and branched aldehydes and gave nitro alcohols with high syn diastereoselectivities (90:10 to 99: 1) and high enantioselectivities (85-95 % ee). This reaction was successfully utilized in a straightforward synthesis of (4S,5R)-epi-cytoxazone. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

引用

页码：2894 / 2897

页数：4

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