title: Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues.
abstract: Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogues in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF(3)-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biological interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization.
authors.affiliation: Chimie ParisTech, Laboratoire Charles Friedel, (LCF), CNRS, UMR 7223, 11 rue P. et M. Curie, 75231 Paris cedex 05, France.
authors.forename: Farouk
authors.initials: F
authors.lastname: Berhal
authors.forename: Zi
authors.initials: Z
authors.lastname: Wu
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Genet
authors.forename: Tahar
authors.initials: T
authors.lastname: Ayad
authors.forename: Virginie
authors.initials: V
authors.lastname: Ratovelomanana-Vidal