REGIO- AND STEREOSELECTIVE OXIDATIONS OF THE EXOCYCLIC SULFUR ATOM OF TWO ENDOCYCLIC KETENE DITHIOACETALS

REFERENCES

• Walkup , R. D. and Boatman , P. D. Jr. 1990 . Tetrahedron Lett. , 31 : 6961
   Google Scholar
• Walkup , R. D. and Boatman , P. D. Jr. 1993 . Tetrahedron Lett. , 34 : 2417
   Google Scholar
• Block , E. 1980 . “The Chemistry of Ethers, Alcohols, and Their Sulfur Analogues” , Edited by: Patai , S. 539 NY : J.S. Wiley . For a review on oxidations of sulfides, see
   Google Scholar
• Pitchen , P. , Dunach , E. , Deshmukh , M. N. and Kagan , H. B. 1984 . J. Am. Chem. Soc. , 106 : 8188 For recent reports of stereoselective oxidations of sulfoxides using asymmetric oxidizing agents, see
   Web of Science ®Google Scholar
• Davis , F. A. and Lal , S. G. 1988 . J. Org. Chem. , 53 : 5004
   Web of Science ®Google Scholar
• Andersen , K. K. 1988 . “The Chemistry of Sulphones and Sulphoxides” , Edited by: Patai , S. , Rappoport , Z. and Stirling , C. 55 NY : J.S. Wiley .
   Google Scholar
• Davis , F. A. , Reddy , R. Thimma and Weismiller , M. C. 1989 . J. Am. Chem. Soc. , 111 : 5964
   Web of Science ®Google Scholar
• Conte , V. , Di Furia , F. , Licini , G. and Modena , G. 1989 . Tetrahedron Lett. , 30 : 4859
   Web of Science ®Google Scholar
• Sakuraba , H. , Natori , K. and Tanaka , Y. 1991 . J. Org. Chem. , 56 : 4124
   Web of Science ®Google Scholar
• Corich , M. , Di Furia , F. , Licini , G. and Modena , G. 1992 . Tetrahedron Lett. , 33 : 3043 and references therein
   Google Scholar
• Breitschuh , R. and Seebach , D. 1992 . Synthesis , : 83 For reports of the oxidations of acyclic sulfides by asymmetric oxidizing agents, where a chiral center in the substrate directed the stereoselectivity to afford diastereomer ratios on the order of 2:1 to 3:1, see
   Google Scholar
• Wnuk , S. F. , Dalley , N. K. and Robins , M. J. 1993 . J. Org. Chem. , 58 : 111
   Web of Science ®Google Scholar
• The term “endocyclic ketene dithioacetal” refers to ketene dithioacetals in which the carbon-carbon double bond and one of the two sulfur atoms are all part of a ring. Thus endocyclic ketene dithioacetals possess the general structure i, as opposed to non-endocyclic ketene dithioacetals of general structures ii. As discussed in reference 2, endocyclic ketene dithioacetals possess stereo-electronically derived reactivities which are unique from those of non-endocyclic ketene dithioacetals
   Google Scholar
• The designation of the configuration as syn originates from the conventional usage of the syn/anti terminology for describing diastereomeric relationships in acyclic systems, and considers the products 5 and 7 to be equivalent to the acyclic system iii, where the syn relationship between the sulfoxide chiral center and the chiral center closest to it becomes apparent.
   Google Scholar
• Lawson , K. R. , Singleton , A. and Whitham , G. H. 1984 . J. Chem. Soc., Perkin 1 , : 859
   Google Scholar
• Grieco , P. A. 1991 . Aldrichimica Acta , 24 : 59
   Google Scholar
• Meyers , A. I. and Walkup , R. D. 1985 . Tetrahedron , 41 : 5089
   Google Scholar
• Meijer , J. , Vermeer , P. and Brandsma , L. 1973 . Rec. Chem. Pays-Bas , 92 : 601
   Google Scholar