Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 31

Journal of the American Chemical Society

Volumn 111, Issue 5, 1989, Pages 1759-1769

  RajanBabu, T V ^a   Fukunaga, Tadamichi ^a   Reddy, G S ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000751449     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00187a031     Document Type: Article

References (26)

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4. Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Pergamon Press: New York, 1980; Vol. 1. (b) For a compilation of other relevant references, see: Park, S.-U.; Chung, S.-K.; Newcomb, M. J, Am. Chem. Soc. 1986, 108, 240.
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7. For conformationally rigid systems: (a) Pradhan, S. K.; Kolhe, J. N.; Mistry, J. S. Tetrahedron Lett. 1982, 23, 4481. (b) Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821. (c) RajanBabu, T. V.; Fukunaga, T. J. Am. Chem. Soc. 1989, 111, 296.
8. While our study was in progress, the first example of a free-radical route to cycloalkanes from carbohydrates was reported by Wilcox et al.: (a) Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546. (b) For an elegant application of this chemistry for the synthesis of pseudo-fructose see: Wilcox, C. S.; Gaudino, J. J. J. Am. Chem. Soc. 1986, 108, 3102. For examples of radical-based pyranoside annulations: (c) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116. (d) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 8102. However, these systems involve the use of primary radicals, and the stereochemical questions we are addressing are not relevant to these cases.
9. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574. (b) In all radical cyclizations reported here using the Barton intermediate, varying amounts of starting alcohols were isolated. We have since found that the Robins procedure is considerably better in some cases: Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059.
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12. 13C methods see ref 12c.
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14. Ample precedent exists in the literature to suggest that this ready equilibration is possible only if the acetoxy and hydroxymethyl groups are cis to one another. (a) Jones, G.; Raphael, R. A.; Wright, S. J. Chem. Soc., Perkin Trans. 1 1974, 1676. (b) Doria, G.; Gaio, P.; Gandolfi, C. Tetrahedron Lett. 1972, 4307.
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21. This effect, which was originally recognized by Beckwith, has since been used in synthesis: (a) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (b) Ueno, Y.; Moriya, O.; Chino, K.; Watanabe, M.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351. (c) Little, R. D.; Wolin, R. L. Abstract of Papers, 193rd National Meeting of the American Chemical Society, Denver, CO; American Chemical Society: Washington, DC, 1987; ORGN 134.
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23. Auge, J.; David, S. Tetrahedron 1984, 40, 2101.
24. For a critical evaluation of the effect of allylic substituents on the stereochemistry of electrophilic additions to olefins, see: Vedejs, E.; McClure, C. K. J. Am. Chem. Soc. 1986, 108, 1094, and references cited therein.
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