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.
|Titolo:||Enantiomerically Pure Bithiophene Diphosphine Oxides as Catalysts for Direct Double Aldol Reactions|
GENONI, ANDREA (Primo)
BENAGLIA, MAURIZIO (Corresponding)
ROSSI, SERGIO (Penultimo)
|Parole Chiave:||aldol reaction; Lewis bases; organocatalysis; stereoselectivity; tetrachlorosilane|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2013|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/chir.22190|
|Appare nelle tipologie:||01 - Articolo su periodico|