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(R)-[(2-Oxo-4-thiazolidinyl)methyl]triphenylphosphonium Iodide: A Wittig Reagent for the Synthesis of Cysteine-Derived Alkenes

  作者 SHAFFER CHRISTINA J; FAN RULIN; LEWIS MICHAEL D; KOWALCZYK JAMES J  
  选自 期刊  Synthesis;  卷期  2011年-23;  页码  3859-3865  
  关联知识点  
 

[摘要](R)-[(2-Oxo-4-thiazolidinyl)methyl]triphenylphosphonium iodide (1), readily prepared in five steps from L-cysteine ethyl ester (39% overall on a 500 g scale), is a useful Wittig reagent for the synthesis of cysteine-derived alkenes such as those found in dipeptide isosteres and peptidomimetics. Preparation of 1 and its use in Wittig olefination reactions with aldehydes is described. The resulting thiazolidinone compounds are readily unmasked to provide the corresponding thiol, symmetrical disulfide, or S-trityl derivatives.

 
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