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Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C-H Activation

Denise A. Colby, Robert G. Bergman* and Jonathan A. Ellman*

*Department of Chemistry, University of California, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California, 94720, Email: rbergmanberkeley.edu, jellmanuclink.berkeley.edu

D. A. Colby, R. G. Berman, J. A. Ellman, J. Am. Chem. Soc., 2008, 130, 3645-3651.

DOI: 10.1021/ja7104784 (free Supporting Information)


Abstract

A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence allows the synthesis of highly substituted pyridine derivatives from alkynes and α,β-unsaturated N-benzyl aldimines and ketimines. The reaction proceeds through dihydropyridine intermediates.

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Key Words

Pyridines


ID: J48-Y2008-0720