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Synlett 1997; 1997(2): 185-186
DOI: 10.1055/s-1997-749
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Stereoselective Synthesis of 2,3-cis-2-Alkyl-5-oxo-3-silyloxycyclopentanecarboxylates using Dirhodium(II)-catalyzed Intramolecular C-H Insertion Reaction of 2-Diazo-3-oxo-5-silyloxyalkanoates

Takayuki Yakura, Seiji Yamada, Akiharu Ueki, Masazumi Ikeda*
  • *Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan, Fax +81(75)595-4763
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Publication History

Publication Date:
31 December 2000 (online)

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Dirhodium(II)-catalyzed intramolecular C-H insertion reaction of 5-(tert-butyldimethylsilyloxy)-2-diazo-3-oxoalkanoates in dichloromethane at room temperature gave stereoselectively 2,3-cis-2-alkyl-3-(tert-butyldimethylsilyloxy)-5-oxocyclopentanecarboxylates.

dirhodium(II) tetraacetate - carbon-hydrogen insertion reaction - α-diazoketone - chemoselectivity - stereoselectivity