On the dihydroxylation of cyclic allylic alcohols

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3407-3410

  Donohoe, Timothy J ^a   Garg, Rina ^a   Moore, Peter R ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029880770     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00558-8     Document Type: Article

References (22)

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8. see also Burdisso, M.; Gandolfi, R.; Rastelli, A. Tetrahedron Lett., 1991, 32, 2659.
9. For some representative examples see: Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc., 1990, 112, 9439; Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl., 1995, 34, 2031; Carless, H. A. J.; Malik, S. S. J. Chem. Soc. Chem. Commun., 1995, 2447; Blacker, A. J.; Booth, R. J.; Davies, G. M.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1, 1995, 2861.
10. For some representative examples see: Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc., 1990, 112, 9439; Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl., 1995, 34, 2031; Carless, H. A. J.; Malik, S. S. J. Chem. Soc. Chem. Commun., 1995, 2447; Blacker, A. J.; Booth, R. J.; Davies, G. M.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1, 1995, 2861.
11. For some representative examples see: Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc., 1990, 112, 9439; Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl., 1995, 34, 2031; Carless, H. A. J.; Malik, S. S. J. Chem. Soc. Chem. Commun., 1995, 2447; Blacker, A. J.; Booth, R. J.; Davies, G. M.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1, 1995, 2861.
12. For some representative examples see: Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc., 1990, 112, 9439; Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl., 1995, 34, 2031; Carless, H. A. J.; Malik, S. S. J. Chem. Soc. Chem. Commun., 1995, 2447; Blacker, A. J.; Booth, R. J.; Davies, G. M.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1, 1995, 2861.
13. (i) Ferner, R. J.; Prasad, N. J. Chem. Soc. C, 1967, 1417;
14. (ii) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc. B, 1970, 1374.
15. 4 and 4 e.q NMO in acetone/water (4:1).
16. 3) 170.8, 170.5, 71.30, 69.83, 42.27, 32.82, 27.95, 26.79, 21.45 ppm.
17. It is possible that in these cases electrostatic repulsion between the electronegative oxygen and the osmium tetraoxide contributes to the stereoselectivity see Vedejs, E.; McClure, C. K. J. Am. Chem. Soc., 1986, 108, 1094.
18. Kon. K; Isoe, S. Tetrahedron Lett., 1980, 21, 3399; Smith III, A. B.; Boschelli, D. J. Org. Chem., 1983, 48, 1217; see also-Ref 1(iii).
19. Kon. K; Isoe, S. Tetrahedron Lett., 1980, 21, 3399; Smith III, A. B.; Boschelli, D. J. Org. Chem., 1983, 48, 1217; see also-Ref 1(iii).
20. Rickborn, B.; Chan, J. H. -H. J. Org. Chem., 1967, 32, 3576; Ref 5(ii); see also Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev., 1993, 93, 1307.
21. Rickborn, B.; Chan, J. H. -H. J. Org. Chem., 1967, 32, 3576; Ref 5(ii); see also Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev., 1993, 93, 1307.
22. 2O and 1 eq. alkene (0.05M) in dichloromethane.