TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE(TMSOTF) CATALYZED AMIDOALKYLATION OF SILYLENOLETHERS - STEREOCONTROLLED SYNTHESES OF (+/-)-SEDAMINE AND (+/-)-NORSEDAMINE

被引：35

作者：

PILLI, RA

DIAS, LC

机构：

[1] Universidade Estadual de Campinas, Instituto de Quimica, C. P. 615 13081 Campinas, SP

来源：

SYNTHETIC COMMUNICATIONS | 1991年 / 21卷 / 21期

关键词：

D O I：

10.1080/00397919108055456

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trimethylsilyl trifluoromethanesulfonate(TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl-and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (i)-sedamine (8) is described. © 1991, Taylor & Francis Group, LLC. All rights reserved.

引用

页码：2213 / 2229

页数：17

共 26 条

[1]

BEYERMAN HC, 1956, RECL TRAV CHIM PAY B, V75, P82

[2]

BEYERMAN HC, 1956, RECL TRAV CHIM PAY B, V75, P63

[3] NEW METHOD FOR METHYLATION OF AMINES [J].