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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 3-4
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Original Articles

⊼-Facial Stereoselectivity in Diels-Alder Reaction of Hexacyclo [7.4.2.01,9.03,7.04,14.06,15] Pentadecane-10,12-diene-2,8-dione

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Pages 585-596 | Received 02 Aug 1988, Published online: 23 Oct 2006

References

  • Still , W. C. 1983 . Current Trends in Organic Synthesis Edited by: Nozaki , H. 233 Pergamon Press . in Ed., p.
  • Vedejs , E. , Dolphin , J. M. , Gopinski , D. M. and Mastalerz , H. 1983 . Current Trends in Organic Synthesis Edited by: Nozaki , H. 221 Pergamon Press . in Ed., p.
  • Vedejs , E. , Dent , W. H. III , Gopinski , D. M. and McClure , C. K. 1987 . J. Am. Chem. Soc. , 109 : 5437
  • Mehta , G. and Padma , S. 1987 . J. Am. Chem. Soc. , 109 : 2212
  • Surapaneni , C. R. and Gilardi , R. 1986 . J. Org. Chem. , 51 : 2382
  • Mehta , G. , Srikrishna , A. , Rao , K. S. , Reddy , K. R. , Acharya , K. A. , Puranik , V. G. , Tavale , S. S. and Guru Row , T. N. 1987 . J. Org. Chem. , 52 : 457
  • Zope , U. R. , Dalvi , P. V. and Pandey , B. Unpublished results
  • Coxon , J. M. , O'Connel , M. J. and Steel , P. J. 1987 . J. Org. Chem. , 52 : 4726 Since last few months we have been trying to publish this work in Tetrahedron Letters. Howevers, during this period, a similar work has been reported by.Besides many other differences, the X-ray structure of 3, the fast reaction between 3 and dienophiles and the non-participation of carbonyls in the π-facial stereoselectivity are noteworthy.
  • Kushner , A. S. 1971 . Tetrahedron Lett. , : 3275 To prove the diene from in 3, its Diels-Alder reaction with dimethylacetylene dicarboxylate is reported without any stereochemical assignment.
  • The qualitative yield of photocyclization step was studied at 254, 300 and 350 nm in Srinivasan-Rayonet photochemical reactor in various solvents and best results (98%) were obtained at 300 nm in acetonitrile (1 mg/1 ml conc.)
  • Mehta , G. , Singh , V. K. and Rao , K. S. 1980 . Tetrahedron Lett. , 21 : 1369 An interesting aspect of selectivity between the Diels-Alder reaction of 3 and cyclopentadiene has been reported by
  • Galin , F. Z. , Afonichev , D. D. , Lerman , B. M. , Kazakov , V. P. and Tolstikov , G. A. 1978 . Zh. Org. Chim. , 14 : 2308 Wrong stereoisomer is reported;C. A. 1979, 90: 167625c. J. Org. Chem. (USSR) 1978, 14, 2131.
  • The structure of 3, 12a, 12d has been confirmed by X-ray and is under publication.
  • The reaction of heterodienophiles eg. diethylazodicarboxylate and 1O2 is under investigation. Preliminary results indicate scrambling of π-facial stereoselectivity.
  • Kalo , J. , Vogel , E. and Ginsburg , D. 1977 . Tetrahedron , 33 : 1177
  • Kahn , S. D. and Hehre , W. J. 1987 . J. Am. Chem. Soc. , 109 : 663
  • Hagenbuch , J. P. , Vogel , P. , Pinkerton , A. A. and Schwarzenbach , D. 1981 . Helv. Chim. Acta , 64 : 1818
  • Gleiter , R. and Paquette , L. A. 1983 . Acc. Chem. Res. , 16 : 328
  • Mahaim , C. and Vogel , P. 1982 . Helv. Chim. Acta , 65 : 866
  • Fox , M. A. , Cardona , R. and Kiwiet , N. J. 1987 . J. Org. Chem. , 52 : 1469
  • Braun , F. K. and Houk , K. N. 1985 . J. Am. Chem. Soc. , 107 1971.
  • Angel , E. C. , Fringuelli , F. , Pizzo , F. , Porter , B. , Taticchi , A. and Wenkert , E. 1986 . J. Org. Chem. , 51 : 2642 and citations therein.

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