Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf2O-Mediated Grob Fragmentation: Access to Indolizidines (-)-2091 and (-)-223J

被引：28

作者：

Lemonnier, Gerald ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 21期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

SUBSTITUTED PIPERIDINES; ASYMMETRIC-SYNTHESIS; ENANTIOENRICHED PIPERIDINES; 4+2 CYCLOADDITION; ALKALOIDS; QUINOLIZIDINES; DERIVATIVES; PYRROLIDINE; PYRIDINE; IMINES;

D O I：

10.1021/jo1015344

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe the gamma-amino hydroxide Grob fragmentation of the aza-bicyclo[2.2.2]octene 1 using triflic anhydride as the activating agent. The resulting dihydropyridinium ion can react with a wide variety of Grignard reagents, giving access to 2,3,6-trisubstituted tetrahydropyridines (2) with high regio- and stereoselectivities. This methodology has been applied to the short synthesis of natural indolizidines (-)-2091 (3) and (-)-223J (4).

引用

页码：7465 / 7467

页数：3

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