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Synlett 1994; 1994(12): 1031-1033
DOI: 10.1055/s-1994-23075
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Enantioselective Intramolecular C-H Insertion Reactions of N-Alkyl-N-tert-Butyl-α-Methoxycarbonyl-α-Diazoacetamides Catalyzed by Dirhodium(II) Carboxylates: Catalytic, Asymmetric Construction of 2-Azetidinones

Nobuhide Watanabe* , Masahiro Anada, Shun-ichi Hashimoto, Shiro Ikegami
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan
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Publication Date:
22 March 2002 (online)

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Intramolecular C-H insertion reaction of N-alkyl-N-tert-butyl-α-methoxycarbonyl-α-diazoacetamides has been catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-phenylalaninate] to afford 4-substituted 1-tert-butyl-3-methoxycarbonyl-2-azetidinones with 3,4-cis stereochemistry in up to 74% ee.