Evidence for C(1)-N(2) bond scission in the isomerization of cis-1,3-disubstituted N-b-benzyl-1,2,3,4-tetrahydro-beta-carbolines into their trans diastereomers under acidic conditions

被引：16

作者：

Cox, ED ^{[1
]}

Li, J ^{[1
]}

Hamaker, LK ^{[1
]}

Yu, P ^{[1
]}

Cook, JM ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 21期

关键词：

D O I：

10.1039/cc9960002477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When cis diastereomer 13a was stirred in CF3CO2D the trans isomer 13b was isolated in 90% yield, while treatment of 13a with CF3CO2H-NaBH4 provided a mixture of the C(1)-N(2) cleaved product 14 and the trans isomer 130; this provides the best evidence to date that scission of the C(1)-N(2) bond occurs during epimerization of cis-1,3-disubstituted 1,2,3,4-tetrahydro-beta-carbolines such as 13a into their trans isomers 13b.

引用

页码：2477 / 2478

页数：2

共 5 条

[1] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].