The direct aldol reaction between aryl methyl ketones with aromatic aldehydes in the presence of tetrachlorosilane and a catalytic amount of a chiral bithiophene diphosphine oxide was studied; the product of double aldol addition was isolated as diacetate in good diastereoselectivity (up to 95:5) and enantioselectivities up to 91%. The reaction with heteroaromatic aldehydes was also investigated leading to the corresponding 1,3 diols, in some cases with excellent stereoselectivities. Chirality 25:643-647:, 2013.

Enantiomerically Pure Bithiophene Diphosphine Oxides as Catalysts for Direct Double Aldol Reactions / A. Genoni, M. Benaglia, S. Rossi, G. Celentano. - In: CHIRALITY. - ISSN 0899-0042. - 25:10(2013), pp. 643-647. [10.1002/chir.22190]

Enantiomerically Pure Bithiophene Diphosphine Oxides as Catalysts for Direct Double Aldol Reactions

A. Genoni;M. Benaglia;S. Rossi;G. Celentano
2013

Abstract

The direct aldol reaction between aryl methyl ketones with aromatic aldehydes in the presence of tetrachlorosilane and a catalytic amount of a chiral bithiophene diphosphine oxide was studied; the product of double aldol addition was isolated as diacetate in good diastereoselectivity (up to 95:5) and enantioselectivities up to 91%. The reaction with heteroaromatic aldehydes was also investigated leading to the corresponding 1,3 diols, in some cases with excellent stereoselectivities. Chirality 25:643-647:, 2013.
aldol reaction; Lewis bases; organocatalysis; stereoselectivity; tetrachlorosilane
Settore CHIM/06 - Chimica Organica
CHIRALITY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/228824
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