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READY AVAILABLE CHIRAL AZAPYRIDINOMACROCYCLES N-OXIDES; FIRST RESULTS AS LEWIS BASE CATALYSTS IN ASYMMETRIC ALLYLATION OF p-NITROBENZALDEHYDE

  作者 VEITIA MAITE SYLLAIYARRETA; JOUDAT MOUNIA; WAGNER MATHIEU; FALGUIERES ANNIE; GUY ALAIN; FERROUD CLOTILDE  
  选自 期刊  Heterocycles;  卷期  2011年83-9;  页码  2011-2039  
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[摘要]We report here the straightforward synthesis of the first series of enantiomerically pure azapyridinomacrocycles N-oxides containing a cyclohexyl chiral moiety. These compounds were readily obtained in good overall yields by a convergent synthesis using natural amino acids as starting building blocks and macrocyclisation as the key step. This method is rapid, efficient and suitable for the introduction of various substituents at the macrocyclic skeleton. Finally, the compounds were tested as organocatalysts for the enantioselective allylation of p-nitrobenzaldehyde with allyltrichlorosilane.

 
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