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A Samarium(II)-Mediated, Stereoselective Cyclization for the Synthesis of Azaspirocycles.

  作者 Guazzelli, Giuditta;Duffy, Lorna A.;Procter, David J.;  
  选自 期刊  Organic Letters;  卷期  2008年10-19;  页码  4291-4294  
  关联知识点  
 

[摘要]Unsatd. keto-lactams, e.g. I [X = (CH2)n, n = 1,2], undergo sequential conjugate redn.-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones contg. vicinal, fully substituted stereocenters, e.g. II, with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization.

 
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