- A heterocycle-forming double michael reaction. [5 + 1] annulation route to highly substituted and functionalized piperidines.
A heterocycle-forming double michael reaction. [5 + 1] annulation route to highly substituted and functionalized piperidines.
Organic letters (2001-09-01)
F Hughes, R B Grossman
PMID11529788
RESUMEN
[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.
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