Trialkylamine versus trialkylphosphine: Catalytic conjugate addition of alcohols to alkyl propiolates


The conjugate addition of activated propargylic alcohols to alkyl propiolates is shown to be catalyst-dependent. Whereas trialkylamines catalyze the expected 1,4-adition of the alcohol on the alkynoate to give the β-alkoxyacrylate derivative, the trialkylphosphine-catalyzed reaction affords densely functionalized bicyclic hexahydrofuro[2,3-b]furan derivatives. A mechanistic proposal for the phosphine-catalyzed addition of alcohols to alkyl propiolates according with these observations is presented. © Georg Thieme Verlag Stuttgart.This research was supported by the Spanish Ministerio de Educación y Ciencia and the European Regional Development Fund (CTQ2005-09074-C02-02 and CTQ2008-06806-C02-02), the Spanish MSC ISCIII (RETICS RD06/0020/1046), CSIC (Proyecto ­Intramural Especial 200719) and the Fundación Instituto Canario de Investigación del Cáncer (FICI-G.I.Nº08/2007).Peer Reviewe

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oaioai:digital.csic.es:10261/132610Last time updated on 8/18/2016

This paper was published in Digital.CSIC.

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