A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer.

Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions / S. Rossi, M. Benaglia, A. Genoni, T. Benincori, G. Celentano. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:1(2011), pp. 158-166. [10.1016/j.tet.2010.11.009]

Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions

S. Rossi
Primo
;
M. Benaglia
Secondo
;
A. Genoni;G. Celentano
Ultimo
2011

Abstract

A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/156233
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