title: Enantioselective α-benzoyloxylation of ketones promoted by primary amine catalyst.
abstract: A mixture of 9-amino-(9-deoxy)epi-dihydroquinidine and salicylic acid was able to promote the direct reaction of various cyclohexanones with dibenzoyl peroxide, thus affording the corresponding protected α-hydroxy carbonyl compounds in high yield and enantioselectivity. Interestingly the same catalytic salt was found to be active when 1-indanones derivatives were directly employed in the reaction with dibenzoyl peroxide furnishing chiral 1-oxo-2,3-dihydro-1H-inden-2-yl benzoates in high yields and enantioselectivity. Furthermore their treatment with NaBH(4) gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.
authors.affiliation: Department of Organic Chemistry A. Mangini, Alma Mater Studiorum-University of Bologna, viale Risorgimento 4, I-40136 Bologna, Italy.
authors.forename: Milind S
authors.initials: MS
authors.lastname: Jadhav
authors.forename: Paolo
authors.initials: P
authors.lastname: Righi
authors.forename: Enrico
authors.initials: E
authors.lastname: Marcantoni
authors.forename: Giorgio
authors.initials: G
authors.lastname: Bencivenni