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Synthesis of gamma,delta-Unsaturated Selenoamides via the Seleno-Claisen Rearrangement of in situ Generated Allylic Vinyl Selenides from Selenoamides and Allylic Bromides

  作者 MURAI TOSHIAKI; EZAKA TATSUYA; KATO SHINZI  
  选自 期刊  Synthesis;  卷期  2012年44-20;  页码  3197-3201  
  关联知识点  
 

[摘要]The deprotonation of alpha-monosubstituted selenoamides with LDA followed by allylation gives gamma,delta-unsaturated selenoamides in good to high yields. In the initial step, allylation may take place at the selenium atom of lithium eneselenolates to form allylic vinyl selenides, which then undergo seleno-Claisen rearrangement. As allylic bromides gamma,gamma-disubstituted compounds such as geranyl and neryl bromides could also be used to give products that incorporated tertiary-quaternary stereogenicity with high efficiency.

 
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