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Synlett 1992; 1992(4): 309-310
DOI: 10.1055/s-1992-21350
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Chlorosilane-Mediated 1,2-Addition of Organocuprates to α,β-Unsaturated Aldehydes: A Case of Vinylogous Cram's Rule

Masayuki Arai* , Takashi Nemoto, Yuji Ohashi, Eiichi Nakamura
  • *Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
08 March 2002 (online)

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In the presence of trialkylchlorosilane, addition of a cuprate reagent to α,β-unsaturated γ-alkoxy aldehydes 1 takes place in a 1,2-addition mode with good diastereoselectivity, providing a case of vinylogous Cram's rule.