通过分子内氨基锂化-碳锂化实现烯丙基氨基烯烃的连续环化反应。

Consecutive cyclization of allylaminoalkene by intramolecular aminolithiation-carbolithiation.

作者信息

Tsuchida Susumu, Kaneshige Atsunori, Ogata Tokutaro, Baba Hiromi, Yamamoto Yasutomo, Tomioka Kiyoshi

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

Org Lett. 2008 Aug 21;10(16):3635-8. doi: 10.1021/ol801397v. Epub 2008 Jul 19.

DOI:10.1021/ol801397v

PMID:18642833

Abstract

Consecutive cyclization of allylaminoalkenes by tandem aminolithiation-carbolithiation proceeded smoothly by using a lithium amide as a lithiating agent as well as protonating agent to give bicyclic amines, octahydroindolizine and hexahydro-1 H-pyrrolizine, in reasonably high yield and diastereoselectivity.

摘要

通过使用锂酰胺作为锂化剂以及质子化剂，烯丙基氨基烯烃通过串联氨基锂化-碳锂化进行连续环化反应，能够顺利地生成双环胺、八氢吲哚嗪和六氢-1H-吡咯嗪，产率和非对映选择性都相当高。