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Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide.

  作者 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.;  
  选自 期刊  Organic Letters;  卷期  2008年10-23;  页码  5437-5440  
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[摘要]An exptl. 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 aliph., substituted arom., and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported. E.g., reaction of (EtO)2P(O)CH2CO2CMe3 and cyclohexanecarboxaldehyde in presence of MeMgBr gave 98% a,b-unsatd. ester I (>180:1 E/Z).

 
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