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Synlett 1994; 1994(5): 353-355
DOI: 10.1055/s-1994-22852
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Enantioselective Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-phenylalaninate]: The Effect of the Substituent at the Insertion Site on Enantioselectivity

Shun-ichi Hashimoto* , Nobuhide Watanabe, Shiro Ikegami
  • *Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-01, Japan
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Publication Date:
22 March 2002 (online)

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The enantioselectivity in dirhodium(II) tetrakis[N-phthaloyl-(S) -phenylalaninate]-catalyzed cyclization of α-diazo β-keto 2,4-dimethyl-3-phenyl esters possessing substituted phenyl or vinyl groups at the insertion site was studied. The substituent effects on enhancement of the enantioselectivity were even more pronounced with the vinyl group than with the phenyl group, though 80% ee could be achieved with both of the (E)-conjugated ester and p-trifluoromethanesulfonyloxyphenyl groups.