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A heterocycle-forming double michael reaction. [5 + 1] annulation route to highly substituted and functionalized
1Department of Chemistry, University of Kentucky, Lexington, 40506-0055, USA.
Organic Letters
|September 1, 2001
Abstract:
[reaction: see text]. Nitrogen-containing tethered diacids, easily prepared by reductive alkylation of diethyl aminomalonate or ethyl cyanoglycinate, undergo double Michael reactions with 3-butyn-2-one to give highly functionalized and substituted piperidines (pipecolic acid derivatives) with surprisingly high stereoselectivity. The heterocyclic double Michael adducts can be induced to undergo further cyclizations to give a variety of azabicyclic and diazabicyclic compounds.