Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 21, Pages 7465-7467Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1015344
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Research Chairs
- Canada Foundation for Innovation
- Universite de Montreal
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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).
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