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 NaBH4 gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.

Enantioselective α-Benzoyloxylation of Ketones Promoted by Primary Amine Catalyst

RIGHI, PAOLO;BENCIVENNI, GIORGIO
2012

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 NaBH4 gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.
2012
M. S. Jadhav; P. Righi; E. Marcantoni; G. Bencivenni
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/114199
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