Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols

Journal of the American Chemical Society

Volumn 132, Issue 17, 2010, Pages 5962-5963

  Herrmann, Aaron T ^a   Saito, Tatsuo ^a   Stivala, Craig E ^a   Tom, Janine ^a   Zakarian, Armen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; COMPLEX MOLECULES; HYDROXYL GROUPS; STEREO-SELECTIVE; STEREOCONTROL;

ISOMERS; RHENIUM; SYNTHESIS (CHEMICAL);

RHENIUM COMPOUNDS;

ALCOHOL; RHENIUM;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; THERMODYNAMICS;

CATALYSIS; PROPANOLS; RHENIUM; STEREOISOMERISM;

EID: 77951670046     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101673v     Document Type: Article

References (24)

1. Review: Bellemin-Laponnaz, S. and Le Ny, J. P. C. R. Chimie 2002, 5, 217-224
2. Mo, V, Chabardes, P., Kuntz, E., and Varagnat, J. Tetrahedron 1977, 33, 1775-1783
3. Akai, S., Tanimoto, K., Kanao, Y., Egi, M., Yamamoto, T., and Kita, Y. Angew. Chem., Int. Ed. 2006, 45, 2592-2595
4. Hosogai, T., Fujita, Y., Ninagawa, Y., and Nishida, T. Chem. Lett. 1982, 357-360
5. Matsubara, S., Okazoe, T., Oshima, K., Takai, K., and Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 844-849
6. Belgacem, J., Kress, J., and Osborn, J. A. J. Am. Chem. Soc. 1992, 114, 1501-1502
7. Belgacem, J., Kress, J., and Osborn, J. A. J. Mol. Catal. 1994, 86, 267-285
8. Re(VII)
9. Bellemin-Laponnaz, S., Gisie, H., Le Ny, J. P., and Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 976-978
10. Bellemin-Laponnaz, S., Le Ny, J. P., and Osborn, J. A. Tetrahedron Lett. 2000, 41, 1549-1552 MTO:
11. Jacob, J., Espenson, J. H., Jensen, J. H., and Gordon, M. S. Organometallics 1998, 17, 1835-1840
12. The following reports describe solutions to this problem with certain types of substrate
13. Morrill, C. and Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 2842-2843
14. Morrill, C., Beutner, G. L., and Grubbs, R. H. J. Org. Chem. 2006, 71, 7813-7825
15. Hansen, E. C. and Lee, D. J. Am. Chem. Soc. 2006, 128, 8142-8143
16. For a review of other methods for stereoselective 1,3-diol synthesis, see
17. Hoveyda, A. H., Evans, D. A., and Fu, G. C. Chem. Rev. 1993, 93, 1307-1370
18. 4 form exists in dilute aqueous solutions:
19. Beyer, H., Glemser, O., and Krebs, B. Angew. Chem., Int. Ed. 1968, 7, 295-296
20. Tadpetch, K. and Rychnovsky, S. D. Org. Lett. 2008, 10, 4839-4842
21. Gesinski, M. R., Tadpetch, K., and Rychnovsky, S. D. Org. Lett. 2009, 11, 5342-5345
22. Useful levels of diastereoselectivity (90% or more) were obtained in toluene and THF. See Supporting Information for details.
23. Hutchinson, J. M., Lindsay, H. A., Dormi, S. S., Jones, G. D., Vicic, D. A., and McIntosh, M. C. Org. Lett. 2006, 8, 3663-3665
24. Edwards, P. and Wilkinson, G. J. Chem. Soc., Dalton Trans. 1984, 2695-2712