140184-82-3Relevant academic research and scientific papers
Highly (E)-selective wadsworth-emmons reactions promoted by methylmagnesium bromide
Claridge, Timothy D. W.,Davies, Stephen G.,Lee, James A.,Nicholson, Rebecca L.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Toms, Steven M.
supporting information; experimental part, p. 5437 - 5440 (2009/06/18)
(Chemical Equation Presented) An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.
STEREOSPECIFIC CROSS-COUPLING REACTIONS OF 3-ARYLSULFINYLPROPENOATES WITH ORGANOMETALLIC REAGENTS
Cardellicchio, Cosimo,Cicciomessere, Angela Rosa,Naso, Francesco,Tortorella, Paolo
, p. 555 - 558 (2007/10/03)
(E)- or (Z)-3-arylsulfinylpropenoates have been reacted with several organometallic reagents.Grignard reagents were found to promote only the complete substitution of the arylsulfinyl group in good yields (up to 92percent).The reaction followed a stereochemical course of retention of configuration with high values of stereospecificity (up to 99percent) in most cases.The observation made are discussed in the light of current views concerning nucleophilic substitution at a vinyl carbon atom.The addition-elimination pathway is considered valid, whereas a route involving the formation of a sulfurane as an intermediate, followed by a ligand coupling, is considered less likely.
Carbonyl olefination with α-stannyl ester enolates: a new synthesis of α,β-unsaturated esters
Zapata, Antonio,Nunez, Beatriz M.,Ferrer, Fernando J.
, p. C9 - C11 (2007/10/02)
The reaction of α-stannyl ester enolates with carbonyl compounds is described. α,β-Unsaturated esters are obtained in good yields.A reaction mechanism is proposed.
