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. 2003 May 28;125(21):6360-1.
doi: 10.1021/ja0348647.

Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines

Claude Legault  1 , André B Charette
Affiliations

Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines

Claude Legault et al. J Am Chem Soc. .

Abstract

Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.

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