Issue 6, 2014

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Jan 2014
Accepted
27 Feb 2014
First published
27 Feb 2014

Chem. Sci., 2014,5, 2438-2442

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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