On the Antarafacial Stereochemistry of the Thermal [1,7]-Sigmatropic Hydrogen Shift

Journal of the American Chemical Society

Volumn 107, Issue 1, 1985, Pages 268-270

  Hoeger, Carl A ^a   Okamura, William H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001282465     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00287a058     Document Type: Letter

References (11)

1. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Spangler, C. W. Chem. Rev. 1976, 76, 187.
2. Schlatmann, J. L. M. A.; Pot, J.; Havinga, E. Recl. Trav. Chim. Pays-Bas 1964, 83, 1173. (b) Hollick, M. F.; Frommer, J.; NcNeill, S.; Richt, N.; Henley, J.; Potts, J. T., Jr. Biochem. Biophys. Res. Commun. 1977, 76, 107.
3. Akhtar, M.; Gibbons, G. J. Tetrahedron Lett. 1965, 509.
4. Sheves, M.; Berman, E.; Mazur, Y.; Zaretskii, Z. J. Am. Chem. Soc. 1979, 101, 1882. (b) Moriarty, R. M.; Paaren, H. E. Tetrahedron Lett. 1980, 2389.
5. Roth, W. R.; König, J.; Stein, K. Chem. Ber. 1970, 103, 426.
6. Hammond, M. L.; Mourino, A.; Okamura, W. H. J. Am. Chem. Soc. 1978, 100, 4907. (b) Condran, P. C., Jr.; Hammond, M. L.; Mouriño, A.; Okamura, W. H. J. Am. Chem. Soc. 1980, 102, 6259. (c) For references to related derivatives, see Onisko, B. L.; Schnoes, H. K.; DeLuca, H. F. J. Org. Chem. 1978, 43, 3441. Okamura, W. H. Acc. Chem. Res. 1983, 16, 81.
7. 3SiI, see: Schmidt, A. H. Aldrichimica Acta 1981, 14, 31 and references therein. (c) Kruerke, U. Chem. Ber. 1962, 95, 174. (d) Schmidt, A. H.; Russ, M. Chem.-Ztg. 1978, 102, 26, 65.
8. Reich, H. J. Acc. Chem. Res. 1979, 12, 22. (b) Reich, H. J.; Wollowitz, S. W.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697. (c) Johnston, A. D. Ph.D. Thesis, University of California, Riverside, 1983. Early work on this conversion was also carried out by Dr. Antonio Mouriño.
9. In addition, a small amount of the 14β, 15β-dideuterio alcohol was formed (14α, 15α: 14β, 15β = 37:1). For recent related cases of hydroxyl-directed catalytic reductions, see the following: (a) Thompson, H. W.; McPherson, E. J. Am. Chem. Soc. 1974, 96, 6232. (b) Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072. (c) Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681. (d) Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 26, 149. (e) Evans, D. A.; Morissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866.
10. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
11. This is paper 28 in the series Studies on Vitamin D (Calciferol) and Its Analogues. For paper 27, see: Jeganathan, S.; Johnston, A. D.; Kuenzel, E. A.; Norman, A. W.; Okamura, W. H. J. Org. Chem. 1984, 49, 2152.