Tetrahedron Letters

A short enantioselective synthesis of (−)-bestatin via l-proline-catalyzed α-amination of an aldehyde

S George, GS Suryavanshi, A Sudalai

文献索引：George, Shyla; Suryavanshi, Gurunath S.; Sudalai, Arumugam Tetrahedron Letters, 2008 , vol. 49, # 48 p. 6791 - 6793

全文：HTML全文

被引用次数: 8

摘要

A short and high yielding enantioselective synthesis of (−)-bestatin, a naturally occurring aminopeptidase inhibitor, is described via l-proline-catalyzed asymmetric α-amination of 3- phenylpropionaldehyde as the key reaction. The methodology also involves a Pd-catalyzed intramolecular cyclization of an allylic acetate giving a trans-oxazoline in a highly diastereoselective manner (dr> 14: 1).