Enantioselective Gold(I)-catalyzed vinylogous [3 + 2] cycloaddition between vinyldiazoacetates and enol ethers.

Abstract

The reaction of vinyldiazoacetates with enol ethers catalyzed by the binuclear gold complex (R)-DTBMSegphos(AuCl)2 activated by silver hexafluoroantimonate results in a highly enantioselective [3 + 2] cycloaddition. The [3 + 2] cycloaddition proceeds with dynamic kinetic resolution when the enol ether is a 4-substituted 1-(methoxymethylene)cyclohexane. The reaction is initiated by nucleophilic attack of the vinyl ethers at the vinylogous position of the gold vinylcarbene intermediate.

DOI: 10.1021/ja407179c

2 Figures and Tables

Cite this paper

@article{Briones2013EnantioselectiveGV, title={Enantioselective Gold(I)-catalyzed vinylogous [3 + 2] cycloaddition between vinyldiazoacetates and enol ethers.}, author={John F Briones and Huw M L Davies}, journal={Journal of the American Chemical Society}, year={2013}, volume={135 36}, pages={13314-7} }