Enantioselective chlorinative aldol reaction of α-substituted acroleins catalyzed by chiral phosphine oxides

被引：5

作者：

Kotani, Shunsuke ^{[1
,2
]}

Hanamure, Takuya ^{[1
]}

Nozaki, Hirono ^{[1
]}

Sugiura, Masaharu ^{[1
]}

Nakajima, Makoto ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

[2] Kumamoto Univ, Prior Org Innovat & Excellence, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 02期

关键词：

TANDEM CONJUGATE ADDITION; ALPHA; BETA-ACETYLENIC KETONES; 1,4-ADDITION-ALDOL REACTION; TRICHLOROSILYL TRIFLATE; TERTIARY AMINE; ALLENIC ESTERS; HYDRIDE DONOR; LEWIS-BASES; ALDEHYDES; COMPLEXES;

D O I：

10.1016/j.tetasy.2017.01.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective chlorinative aldol reaction of a-substituted acroleins with aldehydes catalyzed by chiral phosphine oxides is described. A hypervalent silicon complex-derived chloride adds to the alpha-substituted acroleins to form the corresponding silyl enol ethers in situ, which subsequently reacts with aldehydes to produce the alpha-chloromethyl aldol adducts bearing a quaternary stereogenic center in good yields and stereoselectivities. When activated by a phosphine oxide catalyst, trichlorosilyl triflate acts as an effective promoter for the chlorinative aldol reaction as well as the chloride source; this discovery enabled the enantioselective chlorinative aldol reaction of alpha-substituted acroleins. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：282 / 287

页数：6

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