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Synlett 1996; 1996(4): 399-400
DOI: 10.1055/s-1996-5424
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First Synthesis of Methyl syn 3-CF3-Isoserinate

Ahmed Abouabdellah, Jean-Pierre Bégué* , Danièle Bonnet-Delpon
  • *CNRS, URA 1843, Centre d’Etudes Pharmaceutiques, Rue J.B. Clément, 92296 Chatenay-Malabry, France, Fax: 33 1 46 83 57 40; E-mail: begue@psisun.u-psud.fr
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Publication History

Publication Date:
31 December 2000 (online)

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A [2+2] cycloaddition of the trifluoromethyl aldimines 5 with a ketene provided stereoselectively the CF3-substituted β-lactam 4 in a 50 % yield. Further steps of ring opening and deprotections led to the methyl syn-3-CF3-isoserinate which is a new fluoro analogue of the C-13 side-chain of taxoids.

β-lactam - isoserine - trifluoromethyl compounds - taxol - imine cycloaddition