一种通过铑催化的分子内C-H插入反应从α-氨基酸合成手性γ-内酰胺的新路线。

A novel synthetic route to chiral gamma-lactams from alpha-amino acids via Rh-catalyzed intramolecular C-H insertion.

作者信息

Yoon Cheol Hwan, Flanigan David L, Chong Byong-Don, Jung Kyung Woon

机构信息

Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620-5250, USA.

出版信息

J Org Chem. 2002 Sep 6;67(18):6582-4. doi: 10.1021/jo0259717.

DOI:10.1021/jo0259717

PMID:12201790

Abstract

Highly functionalized gamma-lactams are key intermediates for the synthesis of numerous biologically significant natural products. We herein described the synthesis of various chiral gamma-lactams via intramolecular C-H insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides derived from alpha-amino acids, which possess various functional groups. The cyclizations were highly regio- and stereoselective to afford chiral gamma-lactam motifs in high yields.

摘要

高度官能化的γ-内酰胺是合成众多具有生物学意义的天然产物的关键中间体。我们在此描述了通过源自α-氨基酸的α-重氮-α-(苯磺酰基)乙酰胺的分子内C-H插入反应合成各种手性γ-内酰胺，这些α-氨基酸含有各种官能团。环化反应具有高度的区域选择性和立体选择性，能够以高产率得到手性γ-内酰胺结构单元。