Chiral Bronsted acid-catalyzed regio- and enantioselective arylation of α,β-unsaturated trifluoromethyl ketones

被引：25

作者：

Pei, Zeng-kai ^{[1
]}

Zheng, Yan ^{[1
]}

Nie, Jing ^{[1
]}

Ma, Jun-An ^{[1
]}

机构：

[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 35期

关键词：

Chiral phosphoric acid; Arylation; alpha; beta-Unsaturated trifluoromethyl ketones; Reduction; Enantioselectivity; FRIEDEL-CRAFTS ALKYLATION; INDOLE ALKYLATIONS; PHOSPHORIC-ACID; COMPLEXES;

D O I：

10.1016/j.tetlet.2010.06.132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The interesting examples of chiral phosphoric acid-catalyzed regio- and enantioselective arylation of alpha,beta-unsaturated trifluoromethyl ketones were reported. The reaction proceeded well and the desired products were obtained in good yields (up to 99%) with moderate to good enantioselectivities (up to 88% ee). Several desired products were obtained with excellent optical purities after a single recrystallization. Subsequent reduction of enantiopure products with NaBH4 afforded two diastereomers of chiral trifluoromethyl-substituted secondary alcohols with high enantioselectivities (98% ee). (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4658 / 4661

页数：4

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