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OPPI BRIEFS

STEREOSELECTIVE REDUCTION OF PIVALOYLOXYMETHYL (2S,5R,6S)-6-ACETYL-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE WITH SODIUM BOROHYDRIDE

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Pages 48-51 | Received 08 Jul 1991, Published online: 18 Feb 2009

References

  • Gregory , G. I. 1981 . “Recent Advances in the Chemistry of β-Lactams” , London : The Royal Society of Chemistry . See for example: A. G. Brown and S. M. Roberts, “Recent Advances in the Chemistry of β-Lactams”, The Royal Society of Chemistry, London, 1985
  • Perrone , E. 1988 . Il Farmaco (Pavia) , 43 : 1075 and references cited therein
  • Karaday , S. 1981 . J. Am. Chem. Soc. , 103 : 6765 b) T. N. Salzmann et al., ibid., 102, 6161 (1980). c) A. Yoshida et al., Chem. Pharm. Bull. Japan, 29, 2899 (1981). d) H. Ona et al., ibid., 33, 4382 (1985). e) F. Di Ninno et al., J. Org. Chem., 42, 2960 (1977). f) E. A. Bouffard and T. N. Salzmann, Tetrahedron Lett., 26, 6285 (1985). g) Y. Ito et al., ibid., 27, 5751(1986). h) R. L. Rosati et al., J. Med. Chem., 33, 291 (1990).
  • Math , S. A. 1990 . J. Chem. Soc., Perkin Trans. I , : 89 – 96 .
  • The stereochemistry at C6 was confirmed by 1H NMR, which showed small vicinal coupling constants, J = 1.7 Hz for the hydrogens H5 and H6, typical of a β-lactam trans configuration
  • Sheehan , J. C. 1978 . J. Org. Chem. , 43 : 4856 The structure was confirmed by comparing the spectral data with those reported for the corresponding 2,2,2-trichloroethylester
  • Bateson , J. H. 1986 . Chem. Comm. , : 1151 See refs. 3a,d,g; b) M. Sato et al., Tetrahedron Lett., 27, 6091 (1986). c) F. Pecquet and J. d'Angelo, ibid., 23, 2777 (1982). d) V. J. Jephcote et al., ibid., 25, 2919 (1984). e) F. A. Bouffard and B. G. Christensen, J. Org. Chem., 46, 2208(1981).
  • Dale , A. J. and Mosher , H. S. 1973 . J. Am. Chem. Soc. , 95 : 512
  • Pfaendler , H. R. 1980 . J. Am. Chem. Soc. , 102 : 2039

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