Lewis acid mediated regioselective ring opening of benzylglycidol with dibenzyl phosphate: Short and attractive synthesis of dihydroxyacetone phosphate

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4347-4350

  Meyer, Odile ^a   Ponaire, Sarah ^a   Rohmer, Michel ^a   Grosdemange Billiard, Catherine ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749010576     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061748a     Document Type: Article

References (26)

1. (a) Mitsunobu, O. InComprehensive Organic Synthesis; Trost, B. M., Fleming, L., Pattenden, G., Eds.; Pergamon Press: Oxford, 1990; Vol. 6, pp 88-93.
2. (b) Birkinshaw, T. N. In Comprehensive Organic Functionnal Group Transformations; Katritsky, A. R., Meth-Cohn, O., Rees, C. W., Roberts, S. M., Eds; Pergamon Press: Oxford, 1990; Vol. 1, pp 204-220.
3. (a) Lees, W. J.; Whitesides, G. M. J. Org. Chem. 1993, 58, 1887-1894.
4. (b) Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365-5422.
5. (c) van Herk, T.; Hartog, A. F.; Schoemaker, H. E.; Wever, R. J. Org. Chem. 2006, 71, 6244-6247.
6. Hanson, R. M. Chem. Rev. 1991, 91, 437-474.
7. Lampson, G. P.; Lardy, H. A. J. Biol. Chem. 1949, 181, 697-700.
8. (a) Pederson, R. L.; Liu, K. K.-C.; Rutan, J. F.; Chen, L.; Wong, C.-H. J. Org. Chem. 1990, 55, 4897-4901.
9. (b) Guérard, C.; Alphand, V.; Archelas, A.; Demuynck, C.; Hecquet, L.; Furstoss, R.; Bolte, J. Eur. J. Org. Chem. 1999, 3399-3402.
10. Williamson, R. M.; Pietersma, A. L.; Jameson, G. B.; Parker, E. J. Bioorg. Med. Chem. Lett. 2005, 15, 2339-2342.
11. Roussev, C. D.; Simeonov, M. F.; Petkov, D. D. J. Org. Chem. 1997, 62, 5238-5240.
12. Charmantray, F.; Dellis, P.; Samreth, S.; Hecquet, L. Tetrahedron Lett. 2006, 47, 3261-3265.
13. (a) Chan, T.-H.; Di Raddo, P. Tetrahedron Lett. 1979, 22, 1947-1950.
14. (b) Di Raddo, P.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1983, 16-17.
15. (a) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545-9554.
16. (b) Hunt, D. K.; Seeberger, H. Org. Lett. 2002, 4, 2751-2754.
17. (a) Adelt, S.; Plettenburg, O.; Stricker, R.; Reiser, G.; Altenbach, H.-J.; Vogel, G. J. Med. Chem. 1999, 42, 1262-1273.
18. (b) Plettenburg, O.; Adelt, S.; Vogel, G.; Altenbach, H.-J. Tetrahedron: Asymmetry 2000, 11, 1057-1061.
19. (c) Podeschwa, M. A. L.; Plettenburg, O.; Altenbach, H.-J. Eur. J. Org. Chem. 2005, 3101-3115.
20. Meyer, O.; Rohmer, M.; Grosdemange-Billiard, C. Tetrahedron Lett. 2004, 45, 7921-7923.
21. Guivisdalsky, P. N.; Bittman, R. J. Am. Chem. Soc. 1989, 111, 3077-3079.
22. Bonini, C.; Chiummiento, L.; Lopardo, M. T.; Pullez, M.; Colobert, F.; Solladié, G. Tetrahedron Lett. 2003, 44, 2695-2697.
23. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560-1563.
24. See the Supporting Information.
25. Bonini, C.; Righi, G. Synthesis 1994, 225-238.
26. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13-19.