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Phosphine-Catalyzed Allylic Substitution of Morita−Baylis−Hillman Acetates:  Synthesis of N-Protected β-Aminophosphonic Acid Esters

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journal contribution
posted on 29.09.2006 by HaeIl Park, Chang-Woo Cho, Michael J. Krische
A series of N-protected β-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem SN2‘−SN2‘ mechanism.