三氟甲基醛亚胺的立体选择性巴比耶型烯丙基化反应

Stereoselective Barbier-type allylation reaction of trifluoromethyl aldimines.

作者信息

Legros Julien, Meyer Franck, Coliboeuf Matthieu, Crousse Benoît, Bonnet-Delpon Danièle, Bégué Jean-Pierre

机构信息

BioCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Châtenay-Malabry 92296 Cedex, France.

出版信息

J Org Chem. 2003 Aug 8;68(16):6444-6. doi: 10.1021/jo034205c.

DOI:10.1021/jo034205c

PMID:12895086

Abstract

Trifluoromethyl aldimines could react, under Barbier conditions in the presence of activated zinc, in DMF at room temperature or in THF at reflux, with various allyl bromides to provide the corresponding homoallylamines. Secondary homoallyl trifluoromethylamines were stereoselectively obtained from the optically active aldimine 12 with an excellent diastereoisomeric excess (98%).

摘要

三氟甲基醛亚胺在巴比耶反应条件下，于室温的N,N-二甲基甲酰胺（DMF）中或回流的四氢呋喃（THF）中，在活性锌存在下，能与各种烯丙基溴反应，生成相应的高烯丙基胺。从光学活性醛亚胺12中立体选择性地获得仲高烯丙基三氟甲基胺，非对映体过量率极高（98%）。