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
收藏
页码：4658 / 4661
页数：4
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