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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 19
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Original Articles

A Convenient Reduction-Oxidation Procedure for the Selective Epimerization at Sulfur of Highly Functionalized, Optically Active Sulfoxides

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Pages 3397-3405 | Received 03 Jul 1989, Published online: 24 Oct 2006

References

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  • Van den Broek , L. A. G. M. , Liskamp , R. M. J. , Colstee , J. H. , Lelieveld , P. , Remacha , M , Vázquez , D. , Ballesta , J. P. G. and Ottenheijm , H. C. J. 1987 . J. Med. Chem. , 30 : 325
  • Ottenheijm , H. C. J. , Liskamp , R. M. J. , Van Nispen , S. P. J. M. , Boots , H. A. and Tijhuis , M. W. 1981 . J. Org. Chem. , 46 : 3273
  • Van den Broek , L. A. G. M. , Lázaro , E. , Fennis , P. J. , Missler , F. A. N. , Lelieveld , P. , Ballesta , J. P. G. and Ottenheijm , H. C. J. Manuscript accepted for publication in J. Med. Chem.
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  • Chasar , D. W. and Pratt , T. M. 1976 . Synthesis , : 262 Originally, the reduction reaction is described to be carried out in benzene; we observed, however, that CH2Cl2 is a more suitable solvent.
  • Castrillón , J. P. A. and Szmant , H. H. 1965 . J. Org. Chem. , 30 : 1338 However, under these reaction conditions 3b, 3d and 3e decomposed. Another procedure studied involves the use of PPh3 in refluxing CCl4 for 2–18 hr:
  • Russel , G. A. and Ochrymowycz , L. A. 1970 . J. Org. Chem. , 35 : 2106
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