Synthesis of bicyclic pyroglutamic acid featuring the Ugi reaction and a unique stereoisomerization at the angular position by Grob fragmentation followed by a transannular ketene [2+2] cycloaddition reaction

被引：18

作者：

Vamos, Mitchell ^{[1
]}

Ozboya, Kerem ^{[1
]}

Kobayashi, Yoshihisa ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

SYNLETT | 2007年 / 10期

关键词：

isonitrile; Ugi reaction; pyroglutamic acid; diastereoselectivity; lactams;

D O I：

10.1055/s-2007-982538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereo isomerization at the angular position of N-acylindoles during basic hydrolysis was discovered to give only the syn-bicyclic pyroglutamic acid, proceeding through a transannular [2+2] cycloaddition of a ketene-ketone intermediate generated by a Grob fragmentation.

引用

页码：1595 / 1599

页数：5