Enantioselective phospha-Michael reaction of diethyl phosphonate with exocyclic α,β-unsaturated benzocyclic ketones catalyzed by a dinuclear zinc-AzePhenol catalyst

The dinuclear zinc complexes as high performance catalysts were used to catalyze phospha-Michael reaction of exocyclic alpha,beta-unsaturated benzocyclic ketones under mild conditions, and the desired products possessing 1-indanones or 1-tetralones skeleton were obtained with excellent enantioselectivities of up to 99%/99% ee and yields of up to 99%. The absolute stereochemistry of the major products catalyzed by (R,R)-L1 was determined to be the (R,R)-configuration by X-ray crystallographic analysis of 3d. A positive nonlinear effect was observed and the possible mechanism was proposed. (C) 2018 Elsevier Ltd. All rights reserved.