金鸡纳生物碱/三甲基铝氟化物组合催化的芳基酮的亲核对映选择性三氟甲基化反应

Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones.

作者信息

Mizuta Satoshi, Shibata Norio, Akiti Surendar, Fujimoto Hiroyuki, Nakamura Shuichi, Toru Takeshi

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

出版信息

Org Lett. 2007 Aug 30;9(18):3707-10. doi: 10.1021/ol701791r. Epub 2007 Aug 10.

DOI:10.1021/ol701791r

PMID:17691734

Abstract

The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee.

摘要

使用鲁佩特-普拉卡什试剂对开链和环状芳基酮进行催化、亲核对映选择性三氟甲基化反应现在已经实现，该反应基于金鸡纳生物碱的溴化铵与四甲基氟化铵的组合，操作简单。该方法可靠且通用。已合成出对映体过量率高达94%的三氟甲基取代的四取代芳基醇。