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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 2
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Original Articles

Regiospecific Synthesis of α-Alkylated Ketones

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Pages 139-145 | Received 31 Aug 1979, Published online: 05 Dec 2006

References

  • House , H. O. 1972 . “ Chapt. 9 ” . In Modern Synthetic Reactions , 2nd Edition , Menlo Park, Calif. : W. A. Benjamin, Inc. .
  • Stork , G. and Hudrlik , P. F. 1968 . J. Am. Chem. Soc. , 90 : 4462 4464
  • House , H. O. , Czuba , L. J. , Gall , M. and Olmstead , H. D. 1969 . J. Org. Chem. , 34 : 2324 H.O. House, M. Gall, and H.D. Olmstead, J. Org. Chem., 36, 2361 (1971)
  • Reich , H. J. , Rusek , J. J. and Olson , R. E. 1979 . J. Am. Chem. Soc. , 101 : 2225 See for a regiospecific assemblage of enol silyl ethers, and footnote 18 of this paper
  • Pereyre , M. and Odic , Y. 1969 . Tetrahedron Lett. , 7 : 505
  • Tardella , P. A. 1969 . Tetrahedron Lett. , 14 : 1117
  • Rathke , M. W. and Lindert , A. 1978 . Syn. Communic. , 8 : 9
  • Pasto , D. J. and Wojtkowski , P. W. 1971 . J. Org. Chem. , 36 : 1790
  • Negishi , E. , Idacavage , M. J. , Di Pasquale , F. and Silveira , A. Jr. 1979 . Tetrahedron Lett. , 10 : 845
  • Hightower , L. E. , Glasgow , L. R. , Stone , K. M. , Albertson , D. A. and Smith , H. A. 1970 . J. Org. Chem. , 35 : 1881
  • Hooz , J. and Bridson , J. N. 1973 . J. Am. Chem. Soc. , 95 : 602
  • Hooz , J. and Bridson , J. N. 1972 . Can. J. Chem. , 50 : 2387
  • Hooz , J. and Gunn , D. M. 1969 . J. Am. Chem. Soc. , 91 : 6195
  • Akiyama , S. and McMaster , D. unpublished results
  • The precise pathway to account for specificity is as yet unclarified. Concerted alkylation of an “ate” complex, and/or alkylation of small14 concentrations of the corresponding Li enolate in equilibrium with an “ate” complex are reasonable possibilities
  • It has previously been shown that alkylation (C6H5CH2Br, n-C4H9Br) of the internal Li enolate of 2-heptanone produces a mixture of regioisomeric monoalkylates and dialkylation products.3,15
  • House , H. O. and Trost , B. M. 1965 . J. Org. Chem. , 30 : 2502
  • Hooz , J. and Linke , S. 1968 . J. Am. Chem. Soc. , 90 : 5936 6891
  • Suzuki , A. , Arase , A. , Matsumoto , H. , Itoh , M. , Brown , H. C. , Rogić , M. M. and Rathke , M. W. 1967 . J. Am. Chem. Soc. , 89 : 5708

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