Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines

Abstract

Allylrhodium species derived from δ-trifluoroboryl β,γ-unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z-alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident. Migrate to create: Allylrhodium species from δ-trifluoroboryl β,γ-unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products with two new stereocenters and a Z-alkene. A chiral diene ligand leads to products with high enantioselectivities; a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident.