三氟甲磺酸催化的吲哚和吡咯的高度立体选择性傅克氨基烷基化反应

Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles.

作者信息

Abid Mohammed, Teixeira Liliana, Török Béla

机构信息

Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, Massachusetts 02125-3393, USA.

出版信息

Org Lett. 2008 Mar 6;10(5):933-5. doi: 10.1021/ol703095d. Epub 2008 Feb 7.

DOI:10.1021/ol703095d

PMID:18254637

Abstract

A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and pyrroles and the subsequent Pd-catalyzed hydrogenolysis of the methylbenzyl group provided the products in high yields and excellent enantioselectivities.

摘要

描述了一种通过吲哚和吡咯的高度立体选择性氨基烷基化反应，简单高效地合成高对映体富集的α-三氟甲基-α-（杂芳基）-甘氨酸衍生物对映体的方法。对映体3,3,3-三氟丙酮酸-α-甲基苄基亚胺与吲哚和吡咯在三氟甲磺酸催化下反应，随后钯催化甲基苄基的氢解反应，以高收率和优异的对映选择性得到产物。