Phosphine oxide catalyzed, tetrachlorosilane mediated enantioselective direct aldol reactions of thioesters
Articolo
Data di Pubblicazione:
2015
Citazione:
Phosphine oxide catalyzed, tetrachlorosilane mediated enantioselective direct aldol reactions of thioesters / S. Rossi, R. Annunziata, F. Cozzi, L. Raimondi. - In: SYNTHESIS. - ISSN 0039-7881. - 47:14(2015), pp. 2113-2124. [10.1055/s-0034-1379914]
Abstract:
The stereoselective direct aldol reaction of S-phenyl thioesters and aromatic aldehydes promoted by tetrachlorosilane was realized for the first time; the proposed mechanism involves the formation of a chiral cationic hypervalent silicon species and requires the presence of catalytic amounts of a Lewis base, like a chiral phosphine oxide. The reaction affords syn -hydroxy thioesters as major isomers in good yields, high diastereoselectivity (up to 99:1), and up to 92% enantiomeric excess. The absolute configuration of the major isomer was established by converting the product into the corresponding -hydroxy ester. The scope of the reaction was also investigated by employing differently substituted thioesters in combination with different aromatic aldehydes.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
asymmetric catalysis; direct aldol reaction; hypercoordinate silicon; phosphine oxides; thioesters
Elenco autori:
S. Rossi, R. Annunziata, F. Cozzi, L. Raimondi
Link alla scheda completa:
Link al Full Text: