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Annulations of Enantioenriched Allenylsilanes with in Situ Generated Iminium Ions: Stereoselective Synthesis of Diverse Heterocycles.

  作者 Brawn, Ryan A.;Panek, James S.;  
  选自 期刊  Organic Letters;  卷期  2009年11-2;  页码  473-476  
  关联知识点  
 

[摘要]Highly enantioenriched allenylsilanes participate in Lewis acid mediated annulations with in situ generated iminium ions derived from tert-Bu carbamate and Me carbamate to selectively form functionalized 4,5-dihydropyrroles I (R = Ph, 2-BrC6H4, cyclohexyl, etc.) and 4,5-dihyrooxazines II, resp. The dihydropyrrole products were further elaborated in a stereocontrolled vinylsilane terminated cyclization with in situ generated oxonium ions, resulting in pyranopyrroles III (R1 = Ph, 4-ClC6H4, PhCH2CH2, etc.).

 
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