10.1039/C5SC00295H

Gold(I)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans

Abstract

Allenamides participate as two-carbon components in an intermolecular [2 + 2 + 2] cycloaddition with alkenes and aldehydes when treated with catalytic amounts of a phosphite gold complex. The reaction is highly regio- and chemoselective, and works with different types of alkenes, including styrenes, enolethers or enamides, as well as with aromatic and aliphatic aldehydes. Accordingly, different types of 2,6- disubstituted tetrahydropyrans can be stereoselectively assembled in a single step from commercial or very accessible starting materialsThis work was supported by the Spanish MINECO (SAF2013-41943-R, SAF2010-20822-C02), the ERDF, the European Research Council (Adv. Grant no. 340055) and the Xunta de Galicia (GRC2013-041). HF acknowledges the Fundação para a Ciência e Tecnologia(Portugal) and POPH/FSE for a PhD grant (SFRH/BD/60214/2009

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oai:minerva.usc.es:10347/13247Last time updated on 2/15/2017

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