Bifunctional thiourea-catalyzed enantioselective double Michael reaction of γ,δ-unsaturated β-ketoester to nitroalkene:: asymmetric synthesis of (-)-epibatidine

被引：159

作者：

Hoashi, Y ^{[1
]}

Yabuta, T ^{[1
]}

Takemoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期

关键词：

thiourea; organocatalyst; Michael reaction; asymmetric synthesis; gamma; delta; -unsaturated beta-ketoester; (-)-epibatidine;

D O I：

10.1016/j.tetlet.2004.10.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of 4-nitrocyclohexanone derivatives has been accomplished by enantio selective double Michael additions of gamma,delta-unsaturated beta-ketoesters to nitroalkenes using a catalytic amount of bifunctional thiourea and TMG. The three contiguous stereogenic centers of the obtained products were constructed with good to high diastereoselectivity and up to 92% ee. The biologically active natural product, (-)-epibatidine, has been synthesized from the intermediate 11a in seven steps in 30% overall yield. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9185 / 9188

页数：4

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