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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 7-8
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Original Articles

Lewis Acid-Mediated Intramolecular Ene Reactions of Alkylidene Malonates and 2-Phosphonoacrylates: A Highly Diastereoselective Approach to Trans-1,2-disubstituted Five-Membered Ring Compounds

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Pages 1281-1290 | Received 05 Oct 1988, Published online: 24 Oct 2006

References

  • Taber , D. F. 1984 . Intramolecular Diels-Alder Reactions and Alder Ene Reactions , Berlin : Springer-Verlag .
  • Oppolzer , W. and Snieckus , V. 1978 . Ang. Chem. Int. Ed. Engl. , 17 : 476
  • Snider , B. B. 1980 . Acc. Chem. Res. , 13 : 426
  • Aubert , C. and Begue , J. P. 1988 . Tetrahedron Lett. , 29 : 1011 L. V. Dunketon and, M. Sasa, Synth. Commun., 1987, 17, 1217, see ref. 1(a); for some recent studies, see: (c)
  • Ghosh , S. K. and Sarkar , T. K. 1986 . Tetrahedron Lett. , 27 : 525
  • Tietze , L. F. and Beifuss , U. 1986 . Tetrahedron Lett. , 27 : 1767 During the progress of this work, Tietze et al reported high diastereoselectivity in the Lewis acid - catalysed ene cyclization of related 1, 7-dienes
  • Cauwberghs , S. , De Clercq , P. J. , Tinant , B. and Declercq , J. P. 1988 . Tetrahedron Lett. , 29 : 2493 and reference cited therein; M. E. Jung and, J. Gervay, ibid, 1988 29, 2429; R. K. Beckman, Jr. and, S. S. Ko, J. Amer. Chem. Soc., 1982, 104, 1033; D. D. Sternbach, D. M. Rossana and, K. D. Onan, Tetrahedron Lett., 1985, 26, 591, For a lively discussion of this effect in related intramolecular Diels-Alder reactions, see
  • Kondo , K. , Takemoto , T. and Ikernone , T. 1962 . Bull. Chem. Soc. Jpn. , 35 : 1899
  • Kennewell , P. D. , Matharu , S. S. , Taylor , J. and Sammy , P. G. 1980 . J. Chem. Soc. (Perk I) , : 2542
  • Oppolzer , W. and Thirring , K. 1982 . J. Amer. Chem. Soc. , 104 : 4987
  • Oppolzer , W. and Battig , K. 1982 . Tetrahedron Lett. , 23 : 4669
  • Snider , B. B. and Philips , G. P. 1983 . J. Org. Chem. , 48 : 3685 For intermolecular ene reactions of 2-phosphonoacrylates, see
  • Castagnino , E. , Corsano , S. and Strappaveccia , G. P. 1985 . Tetrahedron Lett. , 26 : 93 and references cited therein, For the continuing interest in new synthetic organophosphonates, see
  • Oppolzer , W. and Robbiani , C. 1980 . Helv. Chem. Acta , 63 : 2010
  • Oppolzer , W. , Robbiani , C. and Battig , K. 1980 . Helv. Chem. Acta , 63 : 2015
  • Oppolzer , W. , Robbiani , C. and Battig , K. 1984 . Tetrahedron , 40 : 1391
  • This presumably explains the pronounced diastereoselectivity in the Lewis acid-induced ene-cyclizations of 1a 1b, since the thermolytic runs3 always produce the cis diastereoisomers to an extent of ∼ 20%
  • Oppolzer , W. and Mirza , S. 1984 . Helv. Chem. Acta , 67 : 730 731 see footnote in
  • McIntosh , M. and Sifler , A. 1978 . Can. J. Chem. , 56 : 226 This compound is made as a mixture of E- & Z- isomers following the general procedure described
  • Wenkert , E. and Gaoni , Y. 1966 . J. Org. Chem. , 31 : 3809

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