A one-pot, fluoride-promoted Wittig reaction was developed. The reactions of ethyl -bromoacetate with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced ,-unsaturated esters in good to excellent yields and E-stereoselectivity. Under the same conditions, reactions of ethyl -bromopropionate, -bromo acetonitrile, and -bromoacetophenone with aliphatic and aromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced the expected ,-unsaturated derivatives in good E-stereoselectivity. The protocol was extended to semistabilized ylides and applied to the synthesis of some combretastatin analogs.
One-pot, fluoride-promoted wittig reaction / T. Fumagalli, G. Sello, F. Orsini. - In: SYNTHETIC COMMUNICATIONS. - ISSN 0039-7911. - 39:12(2009), pp. PII 911127372.2178-PII 911127372.2195.
|Titolo:||One-pot, fluoride-promoted wittig reaction|
SELLO, GUIDO GIOVANNI (Secondo)
ORSINI, FULVIA (Ultimo)
|Parole Chiave:||Tetra-n-butylammonium fluoride; -unsaturated compounds; Wittig reaction|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2009|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1080/00397910802654633|
|Appare nelle tipologie:||01 - Articolo su periodico|