The first organocatalytic, stereoselective and direct aldol reaction of activated thioesters with aldehydes has been accomplished. The trichlorosilyl ketene thioacetal generated in situ by adding a tertiary amine to a trifluoroethyl thioester in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with different aldehydes, coordinated to as well as activated by the chiral cationic hypervalent silicon species. Starting from a variety of readily available thioesters, this Lewis acid-mediated Lewis base-catalyzed transformation allows the direct synthesis of syn-β-hydroxy thioesters in up to 95% ee.
Organocatalytic stereoselective direct aldol reaction of trifluoroethyl thioesters / S. Rossi, M. Benaglia, F. Cozzi, A. Genoni, T. Benincori. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 353:6(2011 Apr), pp. 848-854.
|Titolo:||Organocatalytic stereoselective direct aldol reaction of trifluoroethyl thioesters|
ROSSI, SERGIO (Primo)
BENAGLIA, MAURIZIO (Secondo)
GENONI, ANDREA (Penultimo)
|Parole Chiave:||aldol reaction; organocatalysis; phosphine oxides; tetrachlorosilane; thioesters|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||apr-2011|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/adsc.201100122|
|Appare nelle tipologie:||01 - Articolo su periodico|