Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf2O-Mediated Grob Fragmentation: Access to Indolizidines (−)-209I and (−)-223J

Herein we describe the γ-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 hi...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-11, Vol.75 (21), p.7465-7467
Main Authors: Lemonnier, Gérald, Charette, André B
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:Herein we describe the γ-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 (−)-209I (3) and (−)-223J (4).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1015344