Issue 9, 2013

Gold(i)-catalyzed enantioselective bromocyclization reactions of allenes

Abstract

The enantioselective bromocyclization of allenes is accomplished through the use of a chiral dinuclear gold complex and/or chiral phosphate anions in the presence of an N-bromolactam as an electrophilic bromine source. This method provides access to heterocyclic vinyl bromides with an allylic stereocenter in excellent yield and enantioselectivity. These enantioenriched vinyl bromides may serve as a handle for further derivatization via cross-coupling reactions.

Graphical abstract: Gold(i)-catalyzed enantioselective bromocyclization reactions of allenes

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Mar 2013
Accepted
30 Jun 2013
First published
05 Jul 2013

Chem. Sci., 2013,4, 3427-3431

Gold(I)-catalyzed enantioselective bromocyclization reactions of allenes

D. H. Miles, M. Veguillas and F. D. Toste, Chem. Sci., 2013, 4, 3427 DOI: 10.1039/C3SC50811K

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