Highly diastereoselective radical cyclization of a glucose-derived enol ether radical cation/phosphate anion pair

Tetrahedron Asymmetry

Volumn 14, Issue 19, 2003, Pages 2861-2864

  Crich, David ^a   Suk, Dae Hwan ^a   Sun, Sanxing ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; ANION; BUTYLTIN DERIVATIVE; CATION; ETHER DERIVATIVE; GLUCOSE; GLUCOSE DERIVATIVE; MANNOSE; PHOSPHATE; SELENIDE; TRIBUTYLTIN HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DECOMPOSITION; DIASTEREOISOMER; ISOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; RADICAL REACTION; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 1842578434     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00538-X     Document Type: Article

References (26)

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2. For reviews, see: (a) Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. Chem. Rev. 1997, 97, 3273-3312; (b) Crich, D. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp. 188-206.
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8. Crich D., Ranganathan K., Huang X. Org. Lett. 3:2001;1917-1919.
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10. For reviews on the oxidative approach to alkene radical cations, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chemistry; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, pp. 77-124; (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378; (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
11. For reviews on the oxidative approach to alkene radical cations, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chemistry; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, pp. 77-124; (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378; (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
12. For reviews on the oxidative approach to alkene radical cations, see: (a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chemistry; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, pp. 77-124; (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371-378; (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589.
13. Crich D., Ranganathan K. J. Am. Chem. Soc. 124:2002;12422-12423.
14. Crich D., Gastaldi S. Tetrahedron Lett. 39:1998;9377-9380.
15. Horner J.H., Taxil E., Newcomb M. J. Am. Chem. Soc. 124:2002;5402-5410.
16. 6.
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18. 8PSe: C, 60.09; H, 4.89; Found: C, 60.56; H, 5.56.
19. Acetobromomannose was prepared according to the literature method: Talley E.A., Reynolds D.D., Evans W.L. J. Am. Chem. Soc. 65:1943;575-582.
20. 8PSe: C, 60.09; H, 4.89; Found: C, 60. 28; H, 5.01.
21. 4: C, 70.06; H, 6.61; Found: C, 69.71; H, 6.62.
22. Beckwith A.L.J., Schiesser C.H. Tetrahedron. 41:1985;3925-3941.
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24. For the formation of cyclobutanes in the intermolecular addition of alkene radical cations to alkenes see Ref. 4b.
25. For a discussion of the rearrangement of 2-O-phosphatoxy-anomeric radicals, see: (a) Crich, D.; Yao, Q. J. Am. Chem. Soc. 1993, 115, 1165-1166; (b) Koch, A.; Giese, B. Helv. Chim. Acta 1993, 76, 1687-1701.
26. For a discussion of the rearrangement of 2-O-phosphatoxy-anomeric radicals, see: (a) Crich, D.; Yao, Q. J. Am. Chem. Soc. 1993, 115, 1165-1166; (b) Koch, A.; Giese, B. Helv. Chim. Acta 1993, 76, 1687-1701.