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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 12
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Original Articles

A New Method for the α-Vinylation of Protected α-Amino Acids; Ethylene Oxide as Vinyl Cation Equivalent

Pages 1819-1829 | Received 23 Mar 1990, Published online: 24 Oct 2006

References

  • Harvard University Traveling Scholar at the ETH in Zurich. Current address: Department of Chemistry , New Haven, CT, , U. S. A. : Yale University . P. O. Box 6666, 06511
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  • Tendler , S. J. B. , Threadgill , M. D. and Tisdale , M. J. 1987 . J. Chem. Soc. Perkin Trans. I , : 2617 For an example of competitive inhibition with α-vinylserine see
  • Metcalf , B. W. and Bonilavri , E. 1978 . J. Chem. Soc. Chem. Commun. , : 914 For α-vinylation approaches see
  • Steglich , W. and Wegmann , H. 1980 . Synthesis , : 481
  • Sawada , S. , Nakayama , T. , Esaki , N. , Tanaka , H. , Soda , K. and Hill , R. K. 1986 . J. Org. Chem. , 51 : 3384
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  • Metcalf , B. W. and Jund , K. 1978 . Ibid. , : 3689
  • Greenlee , W. J. , Taub , D. and Patchett , A. A. 1978 . Ibid , : 3999
  • Castelhano , A. L. , Home , S. , Billedeau , R. and Krantz , A. 1986 . Ibid. , 27 : 2435
  • Munster , P. and Steglich , W. 1987 . Synthesis , : 223
  • Castelhano , A. L. , Home , S. , Taylor , G. J. , Billedeau , R. and Krantz , A. 1988 . Tetrahedron , 44 : 5451
  • Vyas , D. M. , Chiang , Y. and Doyle , T. W. 1984 . J. Org. Chem. , 49 : 2037
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  • Pellicciari , R. , Natalini , B. and Marinozzi , M. 1988 . Syn. Commun. , 18 : 1715
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  • Weber , T. , Aeschimann , R. , Maetzke , T. and Seebach , D. 1986 . Helv. Chim. Acta , 69 : 1365 and references 4 and 11
  • There is one report of a direct vinylation of diethyl acetamidomalonate with ethylene and a PdII catalyst (ref. 4). However, the product, a previously well-characterized compound (see ref. 6c), was claimed to be “unstable”
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