Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 13, Pages 5194-5197Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800619m
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Tetrahydropyridines carrying pendant halide functionality at the enamine beta-carbon have been prepared by condensation between appropriately functionalized aldehydes and a vinylogous Mannich adduct. Those enamines display divergent behavior in radical and Heck reactions. Thus, radical addition takes place in a 5-exo-trig fashion whereas Heck couplings follow a 6-endo-trig pathway. The resulting polycyclic products are obtained with high regio- and stereoselectivity.
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