Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol
Colton R. Davis, Irungu K. Luvaga, Joseph M. Ready
Abstract
Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.
Topics & Concepts
ChemistryEnantioselective synthesisStereochemistryCatalysisOrganic chemistryAsymmetric Synthesis and CatalysisOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods