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Stereoselective synthesis of fluorinated β-aminoacids from ethyltrans-N-benzyl-3-trifluoromethylaziridine-2-carboxylate

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
10
Issue
12
Identifiers
DOI: 10.1016/s0957-4166(99)00246-3
Keywords
  • Article
Disciplines
  • Chemistry

Abstract

Abstract trans- N-Benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtainable in enantiopure forms by CAL-catalysed enzymatic resolution, allowed the regio- and stereoselective synthesis of chiral fluorinated anti-α-functionalised-β-aminoacids, such as trifluoroisoserinates or trifluoro-β-alanine, and trans-3-halo- or 3-hydroxy-β-lactams. Starting from the enantiomerically pure methyl analogue of the title compound, 2c, pure enantiomers of trifluoroisoserine can be obtained in high overall chemical yield. Absolute configurations of optically active β-aminoacids were determined by chemical correlation.

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