A heterocycle-forming double michael reaction. [5 + 1] annulation route to highly substituted and functionalized piperidines.
[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.
Hughes
F
F
Department of Chemistry, University of Kentucky, Lexington, 40506-0055, USA.
Grossman
R B
RB
D000478:Alkylation; D008314:Malonates / Q000737:chemistry; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
D008314:Malonates; D010880:Piperidines; C057214:diethyl aminomalonate