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Issue 5, 2015
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Gold(I)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans

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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, enol ethers 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 materials.

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

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Publication details

The article was received on 26 Jan 2015, accepted on 26 Feb 2015 and first published on 02 Mar 2015


Article type: Edge Article
DOI: 10.1039/C5SC00295H
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Citation: Chem. Sci., 2015,6, 2903-2908
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    Gold(I)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans

    H. Faustino, I. Varela, J. L. Mascareñas and F. López, Chem. Sci., 2015, 6, 2903
    DOI: 10.1039/C5SC00295H

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