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. [10.1002/adsc.201100122]

Organocatalytic stereoselective direct aldol reaction of trifluoroethyl thioesters

S. Rossi;M. Benaglia;F. Cozzi;A. Genoni;
2011-04

Abstract

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.
aldol reaction; organocatalysis; phosphine oxides; tetrachlorosilane; thioesters
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/157652
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 53
  • ???jsp.display-item.citation.isi??? 52
social impact