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Issue 6, 2014
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Enantioselective direct α-alkylation of cyclic ketones by means of photo-organocatalysis

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Abstract

We report here the first asymmetric catalytic alkylation of unmodified ketones with alkyl halides. This metal-free approach, which requires light in order to proceed, provides a rare example of highly enantioselective photochemical catalytic processes. An easily available cinchona-based primary amine catalyst guides both the stereoselectivity-defining event and, through the transient formation of photon-absorbing chiral electron donor–acceptor complexes, the photo-activation of the substrates.

Graphical abstract: Enantioselective direct α-alkylation of cyclic ketones by means of photo-organocatalysis

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Publication details

The article was received on 28 Jan 2014, accepted on 27 Feb 2014 and first published on 27 Feb 2014


Article type: Edge Article
DOI: 10.1039/C4SC00315B
Chem. Sci., 2014,5, 2438-2442

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    Enantioselective direct α-alkylation of cyclic ketones by means of photo-organocatalysis

    E. Arceo, A. Bahamonde, G. Bergonzini and P. Melchiorre, Chem. Sci., 2014, 5, 2438
    DOI: 10.1039/C4SC00315B

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