Organocatalyzed Regio- and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent

被引：95

作者：

Furukawa, Tatsuya ^{[1
]}

Nishimine, Takayuki ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Hasegawa, Kimiko ^{[2
]}

Shiro, Motoo ^{[2
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 15期

关键词：

NUCLEOPHILIC TRIFLUOROMETHYLATION; CARBONYL-COMPOUNDS; ASYMMETRIC TRIFLUOROMETHYLATION; SUBSTITUTION; ALKYLATION; 1,4-TRIFLUOROMETHYLATION; CONSTRUCTION; BUTENOLIDES;

D O I：

10.1021/ol201490e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalyzed regioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts using Ruppert-Prakash reagent was achieved in high to excellent yields via a successive S(N)2'/S(N)2' mode for the first time. The reaction was extended to the asymmetric allylic trifluoromethylation by the use of a bis-cinchona alkaloid catalyst with high enantioselectivities up to 94% ee.

引用

页码：3972 / 3975

页数：4

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