Asymmetric Cyclopropanation of Allylic Ethers: Cleavage and Regeneration of the Chiral Auxiliary

Journal of Organic Chemistry

Volumn 58, Issue 4, 1993, Pages 933-936

  Charette, André B ^a   Côté, Bernard ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001315380     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00056a028     Document Type: Article

References (16)

1. Charette, A. B.; Côté, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166–8167.
2. Baer, H. H.; Hernandez, M.; Simesen, L. Carbohydr. Res. 1989, 187, 67–92.
3. For other ring contraction reaction of glucopyranose see: Hanessian, S.; Pernet, A. G. In Advances in Carbohydrate Chemistry and Biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1976; Vol. 33, pp 111–188.
4. Hanessian, S.; Tyler, P. C.; Demailly, G.; Chapleur, Y. J. Am. Chem. Soc. 1981, 103, 6243–6246.
5. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; pp 183–190.
6. Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer Verlag: Berlin, 1983.
7. Binkley, R. W. J. Org. Chem. 1991, 56, 3892–3896.
8. The structure of the α-C-glucofuranoside was unambigously established by converting alcohol 8α into known 2,5-anhydro-1,3,4,6-tetra-O-benzyl-D-mannitol: Kaye, A.; Neidle, S.; Reese, C. B. Tetrahedron Lett. 1988, 29, 1841–1844.
9. The other diastereomer, 2,5-anhydro-1,3,4,6-tetra-O-benzyl-d-glucitol, was compared to the known 2,5-anhydro-d-glucitol derived material: Koerner, T. A. W., Jr.; Voll, R. J.; Younathan, E. S. Carbohydr. Res. 1977, 59, 403–416.
10. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215–1230.
11. Burfield, D. R.; Smithers, R. H. J. Org. Chem. 1978, 43, 3966–3968.
12. 2) from the corresponding 3, 4, 6-tri-O-benzyl-D-glucopyranose: Charette, A. B.; Marcoux, J.-F.; Côté, B. Tetrahedron Lett. 1991, 32, 7215–7218.
13. See also: Crich, D.; Lim, L. B. J. Chem. Soc., Perkin Trans. 1 1991, 2209–2214.
14. Inanaga, J.; Katsuki, J.; Yamaguchi, M. Chem. Lett. 1991, 1025–1026.
15. Hanessian, S.; Girard, C.; Chiara, J. L. Tetrahedron Lett. 1992, 33, 573–576 and references cited therein.
16. Lerous, Jacques; Perlin, A. S. Carbohydr. Res. 1978, 67, 163–178.