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Asymmetric Friedel-Crafts Alkylation of Indoles with Nitrodienes and 2-Propargyloxy-beta-nitrostyrenes Catalyzed by Diphenylamine-Linked Bis(oxazoline)-Zn-(OTf)(2) Complexes

  作者 PENG JIAHUAN; DU DAMING  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-21;  页码  4042-4051  
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[摘要]The catalytic asymmetric FriedelCrafts reaction of indoles with nitrodienes and 2-propargyloxy-beta-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)Zn(OTf)2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89?% ee for nitrodienes and up to 93?% ee for beta-nitrostyrene derivatives). Further transformation of the corresponding FriedelCrafts alkylation product of indole with 2-propargyloxy-beta-nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.

 
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