Organic Letters 2001-09-06

A heterocycle-forming double michael reaction. [5 + 1] annulation route to highly substituted and functionalized piperidines.

F Hughes, R B Grossman

Index: Org. Lett. 3(18) , 2911-4, (2001)

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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.