title: Kinetic resolution of chiral cyclohex-2-enones by rhodium(I)/binap-catalyzed 1,2- and 1,4-additions.
abstract: The feasibility of kinetic resolutions of racemic monosubstituted cyclohex-2-enones by Rh/binap-catalyzed reactions was investigated. 1,2-Addition of AlMe(3) to the 5-substituted derivatives furnished allylic alcohols in the matched case, while the less reactive enantiomers were either left over or transformed into trans-3,5-disubstituted cyclohexanones in parallel or sequential 1,4-additions. Altogether, these represent regiodivergent reactions on racemic mixtures. In contrast, 1,4-addition of aryl groups led to inferior results since either catalyst or substrate control dominated.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, 35032 Marburg, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Kolb
authors.forename: Sebastian
authors.initials: S
authors.lastname: Hirner
authors.forename: Klaus
authors.initials: K
authors.lastname: Harms
authors.forename: Paultheo
authors.initials: P
authors.lastname: von Zezschwitz