The directed dihydroxylation of allylic alcohols

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5027-5030

  Donohoe, Timothy J ^a   Moore, Peter R ^a   Waring, Michael J ^a   Newcombe, Nicholas J ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLYL COMPOUND;

ALCOHOL OXIDATION; ARTICLE; COMPLEX FORMATION; HYDROGEN BOND; HYDROXYLATION; HYPOTHESIS; LOW TEMPERATURE PROCEDURES; STEREOCHEMISTRY;

EID: 0030842941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01061-7     Document Type: Article

References (23)

1. For general references see: (a) Schroeder, M. Chem. Rev., 1980, 80, 187.
2. (b) Lohray, B. B. Tetrahedron: Asymmetry, 1992, 3, 1317.
3. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483.
4. (a) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron Lett., 1983, 24, 3943.
5. (b) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron Lett., 1983, 24, 3947.
6. (c) Cha, J. K.; Christ W. J.; Kishi, Y. Tetrahedron, 1984, 40, 2247.
7. (d) Cha, J. K.; No-Soo Kin, Chem. Rev., 1995, 95, 1761.
8. Xu, D.; Park, C. Y.; Sharpless, K. B. Tetrahedron Lett., 1994, 35, 2495, See also ref 1(c).
9. For references see: Hoveyda, A. H.; Evans D. A.; Fu, G. C. Chem. Rev., 1993, 93, 1307.
10. Johnson, C. R.; Barbachyn, M. R. J. Am. Chem. Soc., 1984, 106, 2459.
11. F. M. Hauser, S. R. Ellenberger, J. Am. Chem. Soc., 1984, 106, 2458: see also Solladié, G.; Fréchou, C.; Demailly, G. Tetrahedron Lett., 1986, 27, 2867.
12. F. M. Hauser, S. R. Ellenberger, J. Am. Chem. Soc., 1984, 106, 2458: see also Solladié, G.; Fréchou, C.; Demailly, G. Tetrahedron Lett., 1986, 27, 2867.
13. Cook, J. M.; Peterson, A. C. J. Org. Chem., 1995, 60, 120.
14. Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc., 1995, 117, 10805.
15. Donohoe, T. J.; Garg, R.; Moore, P. R. Tetrahedron Lett., 1996, 37, 3407.
16. 2 at RT) normally ranges from 50:50 to 60:40 syn:anti, depending on conditions and exact structure of the amine.
17. (a) ref 1(c). See also (b) Kon, K.; Isoe, S. Tetrahedron Lett., 1980, 21, 3399.
18. (c) Smith III, A. B.; Boschelli, D. J. Org. Chem., 1983, 48.
19. 3) 5.10 (1H, t, J= 7.5 Hz), 3.57 (2H, d, J= 5.2 Hz), 3.50 (1H, t, J= 5.2 Hz), 2.05 (2H, br q, J= 7.5 Hz), 1.67 (3H, s), 1.60 (3H, s), 1.60-1.46(2H, m), 1.15 (3H, s).
20. 13C nmr, MS, IR, elemental analysis or HRMS).
21. Carless, H. A, J.; Busia, K.; Dove, Y.; Malik, S. S. J. Chem. Soc., Perkin Transactions 1, 1993, 2505
22. Corey, E. J.; Sarshar, S.; Azimiora, M. D.; Newbold R. C.; Noe, M. C. J. Am. Chem. Soc., 1996, 118, 7851.
23. Nelson, D. W.; Gypser, A.; Pui Tong Ho, Kolb, H. C.; Kondo, T.; Hoi-Lun Kwong; McGrath, D. V.; Rubin, A. E.; Norrby, P-.O.; Gable K. P.; Sharpless, K. B. J Am. Chem. Soc., 1997, 119, 1840, and references therein.