en
Scientific article
Letter
English

Chiral toluene-2,α-sultam auxiliaries: preparation and structure of enantiomerically pure (R)- and (S)-ethyl-2,1′-sultam

Published inTetrahedron Letters, vol. 31, no. 29, p. 4117-4120
Publication date1990
Abstract

Crystalline sultams (R)-2 or (S)-2 were selectively prepared from prochiral saccharine (3) in two steps (53% overall yield) via Ru-(R)-BINAP- or Ru-(S)-BINAP catalyzed asymmetric hydrogenation of imine 4. Alternatively, pure (R)-2 was synthesized (37% overall yield) from (R)-α-phenethylamine in 4–5 steps involving the ortho-sulfination 6→7 and the highly diastereoselective cyclization of sulfinic acid 7 to the sulfinamide 8. X-ray diffraction analyses of sulfinamide 8 and sultam (R)-2 are presented.

Citation (ISO format)
VON OPPOLZER, Wolfgang et al. Chiral toluene-2,α-sultam auxiliaries: preparation and structure of enantiomerically pure (R)- and (S)-ethyl-2,1′-sultam. In: Tetrahedron Letters, 1990, vol. 31, n° 29, p. 4117–4120. doi: 10.1016/S0040-4039(00)97557-9
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ISSN of the journal0040-4039
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