通过对β-三氟甲基-α，β-烯酮的对映选择性傅克烷基化反应，合成具有三氟甲基取代的手性三级碳原子的功能化吲哚。

Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones.

机构信息

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot, València, Spain.

出版信息

Chemistry. 2010 Aug 9;16(30):9117-22. doi: 10.1002/chem.201000568.

DOI:10.1002/chem.201000568

PMID:20583054

Abstract

Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.

摘要

基于 BINOL 的手性配体与叔丁醇锆形成的手性配合物催化吲哚与β-三氟甲基-α,β-不饱和酮的傅-克烷基化反应，得到在三氟甲基上连接不对称三级碳原子的官能化吲哚。该反应可适用于大量取代的α-三氟甲基烯酮和取代的吲哚。预期产物以良好的产率和高达 99%的对映选择性获得。