TRANSITION METAL-CATALYZED RADICAL CYCLIZATIONS - A LOW-TEMPERATURE PROCESS FOR THE CYCLIZATION OF N-PROTECTED N-ALLYLTRICHLOROACETAMIDES TO TRICHLORINATED GAMMA-LACTAMS AND APPLICATION TO THE STEREOSELECTIVE PREPARATION OF BETA,GAMMA-DISUBSTITUTED GAMMA-LACTAMS

被引：136

作者：

NAGASHIMA, H ^{[1
]}

OZAKI, N ^{[1
]}

ISHII, M ^{[1
]}

SEKI, K ^{[1
]}

WASHIYAMA, M ^{[1
]}

ITOH, K ^{[1
]}

机构：

[1] TOYOHASHI UNIV TECHNOL,DEPT MAT SCI,TOYOHASHI,AICHI 441,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 02期

关键词：

D O I：

10.1021/jo00054a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.

引用

页码：464 / 470

页数：7