Regioselective Rhodium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Terminal Alkynes

Org Lett. 2016 Jan 4;18(1):124-7. doi: 10.1021/acs.orglett.5b03391. Epub 2015 Dec 18.

Abstract

A new method for the rhodium-catalyzed regioselective C-C bond formation using terminal alkynes and 1,3-dicarbonyl compounds to achieve valuable branched α-allylated 1,3-dicarbonyl products is reported. With a Rh(I)/DPEphos/p-CF3-benzoic acid as the catalyst system, the desired products can be obtained in good to excellent yields and with perfect regioselectivity. A broad range of functional groups were tolerated, and first experimental insights of a plausible reaction mechanism were obtained.

Publication types

  • Research Support, Non-U.S. Gov't