57415-80-2Relevant articles and documents
STEREOSELECTIVE SYNTHESIS OF DIMETHYL- AND DIETHYL-E-2-(TRIMETHYLSILYL)VINYL PHOSPHONATES AND THEIR USE IN THE DIELS-ALDER REACTION
Maffei, Michel,Buono, Gerard
, p. 297 - 302 (2007/10/02)
Dimethyl E-2-(trimethylsilyl)vinyl phosphonate 1 and diethyl E-2-(trimethylsilyl)vinyl phosphonate 2 are obtained stereoselectively by Pd(0) coupling of an E/Z mixture of (2-trimethylsilyl)vinyl bromide 3 and dimethyl phosphite or diethyl phosphite, respectively.Their use in the Diels-Alder reaction with cyclopentadiene is described, and coordination of aluminum trichloride to the phosphonyl group favors the endo stereoselectivity.Keywords: Vinyl phosphonates; vinyl silanes; palladium-catalyzed carbon-phosphorus bond formation; Diels-Alder reaction; organophosphorus dienophiles; Lewis acids.