Organocatalytic Asymmetric Benzylation and Aldol-Hemiacetalization of α,β-Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4-Dihydroisocoumarins

被引：40

作者：

Duan, Jindian ^{[1
]}

Cheng, Yuyu ^{[1
]}

Cheng, Jing ^{[1
]}

Li, Rou ^{[1
]}

Li, Pengfei ^{[1
]}

机构：

[1] South Univ Sci & Technol China, Dept Chem, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 03期

基金：

中国国家自然科学基金;

关键词：

aldol; enone; isocoumarin; organocatalysis; trifluoromethyl; CHIRAL PRIMARY AMINES; DIELS-ALDER REACTIONS; ALPHA-BENZYLATION; 1H-2-BENZOPYRAN-1-ONE DERIVATIVES; PHARMACOLOGICAL ACTIVITY; CATALYTIC-REACTIONS; CONJUGATE ADDITION; MICROBIAL PRODUCTS; ALDEHYDES; ISOCOUMARINS;

D O I：

10.1002/chem.201604920

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method has been developed for the organocatalytic enantioselective benzylation and aldol-hemiacetalization of alpha,beta-unsaturated trifluoromethyl ketones with toluene derivatives in the presence of a tertiary amine-thiourea catalyst. This method represents a facile and efficient strategy for the asymmetric synthesis of optically active 3,4-dihydroisocoumarins bearing a trifluoromethylated tetrasubstituted carbon stereocenter with high enantioselectivity. Notably, this strategy was used to synthesize several chiral trifluoromethylated analogues of typharin with high efficiency.

引用

页码：519 / 523

页数：5

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