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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 14
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Original Articles

Use of 1-Penten-3-One-4- Phosphonate as a Kinetic Ethyl Vinyl Ketone Equivalent in the Robinson Annulation Reaction1

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Pages 1745-1759 | Published online: 05 Dec 2006

References

  • Suryawanshi , S. N. and Fuchs , P. L. 1986 . J. Org. Chem. , 51 : 902 Bruceantin Support Studies 11. For paper 10 see: For other organophosphorus annulation strategies, see: Pariza, R.J. and Fuchs, P.L., J. Org. Chem., 1985, 50, 4252 and references cited therein
  • Thesis , Ph. D. and Kuo , F. 1986 . Purdue University .
  • Raucher , S. and Koolpe , G. A. 1978 . J. Org. Chem. , 43 : 3794
  • Other more normal bases including NaH, KH, KOtBu, and LDA failed to afford 4 in acceptable yield, see reference 2
  • Mukaiyama , T. 1977 . Angew Chem. Int. Ed. Engl. , 16 : 817
  • Snitman , D. L. , Tsai , M. Y. and Watt , D. S. 1978 . Syn. Comm. , 8 : 195 and references cited therein
  • Jung , M. E. 1976 . Tetrahedron , 32 : 3 For recent review of the Robinson annulation reaction see:
  • Mathey , F. and Savignac , P. 1978 . Tetrahedron , 34 : 649
  • Corey , E. J. and Kwiatkowski , G. T. 1966 . J. Am. Chem. Soc. , 88 : 5654 Substitution of ethyl acrylate (cf. for 7 did not allow a satisfactory synthesis of 8
  • Corey , E. J. , Ohuchida , S. and Hahl , R. 1984 . J. Am. Chem. Soc. , 106 : 3875
  • Wasson , R. L. and House , H. O. 1963 . Org. Synth. Coll. , Vol 4 : 552
  • Wadsworth , W. S. and Emmons , W. D. 1961 . J. Am. Chem. Soc. , 83 : 1733
  • Boutagy , J. and Thomas , R. 1974 . Chem. Rev. , 74 : 87
  • Clark , R. D. , Kozar , L. G. and Heathcock , C. H. 1975 . Syn. Comm. , 5 : 1
  • Piers , E. , Akeysekera , B. and Scheffer , J. R. 1979 . Tet. Lett. , 3279
  • Aristoff , P. A. 1983 . Syn. Comm. , 13 : 145
  • Aristoff , P. A. 1985 . J. Org. Chem. , 50 : 1765 and references cited therein
  • Ohta , S. , Shimabayashi , A. , Hatano , S. and Okamato . 1983 . Synthesis , : 715 Synthesis of cyclohexenones bearing a carboalkoxy moiety in the α-position have been achieved using 4-carboalkoxybute-2-ene-3-one (see and references cited therein)
  • Periff , G. and Courbis , P. 1974 . Can. J. Chem. , 52 : 2894 Three papers cite the preparation of enones substituted by a phosphonate moiety in the α' position: see also references 8 and 9. Two papers have used these phosphonates for intermolecular Wadsworth-Emmons reactions to produce cross-conjugated dienones: See:
  • Motoyoshiya , J. , Miyajima , M. , Hirakawa , K. and Kakurai , T. 1985 . J. Org. Chem. , 50 : 1326
  • C. A. 85 ( 7 ) 46072h
  • Shoolery , J. N. Research & Application Notes , Palo Alto, Ca : Varian NMR Applications Laboratory .
  • Still , W. C. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923
  • Perrin , D. D. , Armarego , W. L.F. and Perrin , D. R. 1980 . Purification of Laboratory Chemicals , 2nd Edition , Pergamon Press .
  • Vedejs , E. , Engler , D. A. and Telschow , J. E. 1978 . J. Org. Chem. , 43 : 188

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