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
收藏
页码：1924 / 1926
页数：3
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