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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 2
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Original Articles

Claisen/Ozonolysis Alternative to Alkylation of Enolate Anions. Synthesis of 1,4-Dicarbonyl Compounds

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Pages 169-182 | Published online: 05 Dec 2006

References

  • Fellow of the Alfred p. Sloan, Foundation, 1981–89; Research Career Development Award recipient, 1984–89; to whom correspondence should be addressed
  • Rosini , G. , Ballini , R. and Sorrenti , P. 1983 . Tetrahedron , 39 : 4127 For leading references concerning syntheses of 1,4 dicarbonyl compounds see:
  • Sharma , K. K. and Torsell , K. B. G. 1984 . Tetrahedron , 40 : 1085
  • Wenkert , E. , Mueller , R. A. , Reardon , E. J. Jr. , Sathe , S. S. , Scharf , D. J. and Tosi , G. 1970 . J. Am. Chem. soc. , 92 : 7428
  • During the synthesis of isocomenic acid (see ref. 6), the preparation of 12 by direct alkylation of an enolate anion with α-bromoacetate proceeded with only 60% yield, whereas the Claisen/ozonolysis sequence affords 12 in comparable yields and without purification problems
  • Martin , S. F. 1980 . Tetrahedron , 36 : 419 For a review of methods amenable to the construction of quaternary centers see:
  • Cresson , P. and Lecour , L. 1966 . C. R. Acad. Sci. C. , 262 : 1157 For applications of ortho-ester Claisen rearrangement in synthesis see: C. R. Acad. Sci. C., 1968, 266, 409; C. R. Acad. Sci. C., 1969, 268, 1535
  • Hudlicky , T. , Kutchan , T. M. , Wilson , S. R. and Mas , D. T. 1980 . J. Am. Chem. Soc. , 102 : 6353 Hudlicky, T.; Koszyk, F. J.; Sheth, J. P., J. org. Chem., 1980, 45, 5020
  • Ireland , R. E. , Mueller , R. H. and Willard , A. K. 1976 . J. Am. Chem. Soc. , 98 : 2868
  • Bennett , G. B. 1977 . Synthesis , : 589
  • Parker , K. A. and Kosley , R. Q. 1975 . Tetrahedron lett. , : 691
  • Babler , J. H. and Tortorello , A. J. 1976 . J. Org. Chem. , 41 : 885
  • Wenkert , E. , McPhearson , C. A. , Sanchez , E. L. and Webb , R. L. 1973 . Syn. Commun. , 3 : 255
  • Short , R. P. , Revol , J. M. , Ranu , B. C. and Hudlicky , T. 1983 . J. Org. Chem. , 48 : 4453

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