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Synfacts 2007(10): 1025-1025  
DOI: 10.1055/s-2007-968980
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Synthesis of Dihydropyridines

Contributor(s): Victor Snieckus, Wei Gan
Z. Sun, S. Yu, Z. Ding, D. Ma*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsdatum:
07. November 2007 (online)

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Significance

A Cu-bisoxazoline catalyzed enantio­selective addition of terminal alkynes to N-acylpyridinum salts is reported. The reaction is quite general, proceeds in good yields and poor to excellent ee without 1,4-addition products observed. A carbonyl functionality at the 3-position of terminal alkynes is essential for achieving high enantioinduction. The dihydropyridine products were further converted into 2,6-cis-disubstituted piperidines.