Diastereoselective synthesis of 1,3-diamines by a domino reaction of imines, enamines, and trichlorosilane

被引：10

作者：

Kashiwagi, Takeru ^{[1
]}

Kotani, Shunsuke ^{[2
]}

Nakajima, Makoto ^{[1
]}

Sugiura, Masaharu ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto 860, Japan

[2] Kumamoto Univ, Prior Org Innovat & Excellence, Kumamoto 860, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 11期

关键词：

1,3-Diamines; Domino reaction; Enamine; Lewis base catalyst; Trichlorosilane; REDUCTIVE ALDOL REACTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; TANDEM CATALYSIS; COMPLEXES; ALKALOIDS; ALDEHYDES; DIAMINES; KETONES; BASES;

D O I：

10.1016/j.tetlet.2014.01.152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we report a new highly diastereoselective domino reaction of imines, enamines, and trichlorosilane. The reaction involves C C bond formation between the imine and enamine followed by the intramolecular reduction of the resulting iminium intermediate by the hydrosilyl group, affording a 1,2-anti-2,3-anti-1,3-diamine in good yield with high diastereoselectivity. Lewis base catalysts such as HMPA increased the chemical yield without decreasing the diastereoselectivity. (c) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1924 / 1926

页数：3

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