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Paper | Regular issue | Vol 29, No. 7, 1989, pp.1283-1292
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4964
Generation and Cyclization of Nitrilium Ions from Amides

Robert E. Gawley* and Sanjay R. Chemburkar

*Department of Chemistry, College of Arts of Sciences, University of Miami, 1301 Memorial Dr., Coral Gables, FL 33124-0431, U.S.A.


Amides are shown to be eflcient precursors to nitrilium ions, which may cyclize onto styryl terminators to form pyrrolines. Comparison of several cyclization substrates defines the steric and stereoelectronic scope and liminations of the process. Appropriately functionalized pyrrolines may be reduced with chiral borohydrides and further elaborated to nonracemic pyrrolizidines and indolizidines.