Water-soluble organometallic catalysts from carbohydrates. 1. Diphosphinite-Rh complexes

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1229-1232

  Shin, Seunghoon ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000624635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908979     Document Type: Article

References (30)

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7. Sugar phosphinites have been used as ligands since 1978. For recent references, see: (a) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eu. J. 1998, 4, 769 and references therein.
8. (b) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis. In Advances in Catalytic Processes, JAI Press: Greenwich, 1997; Vol. 2, pp 1-41.
9. (a) Ni-Catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
10. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
11. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
12. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295.
13. (d) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, in press.
14. (d) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, in press.
15. See, for example: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein.
16. (a) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265, footnote 10. Also ref 3b and: Casalnuovo, A. L.; RajanBabu, T. V. U.S. Patent 5 175 335, 1992.
17. (a) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265, footnote 10. Also ref 3b and: Casalnuovo, A. L.; RajanBabu, T. V. U.S. Patent 5 175 335, 1992.
18. For other recent reports dealing with the use of carbohydrates for solubilizing an organometallic catalyst, see: (a) Beller, M.; Krauter, J. G. E.; Zapf. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 772.
19. (b) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829.
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21. For the synthesis of phosphhine ligands from trehalose see: (a) Brown, J. M.; Cook, S. J.; Kent, A. G. Tetrahedron 1986, 42, 5097.; Gilbertson, S. R.; Chang, C. T. J. Org. Chem. 1995, 60, 6226.
22. For the synthesis of phosphhine ligands from trehalose see: (a) Brown, J. M.; Cook, S. J.; Kent, A. G. Tetrahedron 1986, 42, 5097.; Gilbertson, S. R.; Chang, C. T. J. Org. Chem. 1995, 60, 6226.
23. (b) Just prior to the submission of this manuscript (7/30/1999) a report dealing with the syntheis and applications of phosphinites related to 14 has appeared. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. Our work was presented at the Central Regional ACS Meeting, Columbus, OH, June 21-23, Abstract No. 129.
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27. See the Supporting Information for details.
28. Borns, S.; Kadyrov, R.; Heller, D.; Baumann, W.; Spannenberg, A.; Kempe, R.; Holz, J.; Börner, A. Eur. J. Inorg. Chem. 1998, 1291.
29. 2O. The exact mechanism of this reaction and its stereochemical consequences remain unknown. For related observations, see: Lecomte, L.; Sinou, D.; Bakos, J.; Tóth, I.; Heil, B. J. Organomet. Chem. 1989, 370, 277-284. Laghmari, M.; Sinou, D. J. Mol. Catal. 1991, 66, L15-L18.
30. 2O. The exact mechanism of this reaction and its stereochemical consequences remain unknown. For related observations, see: Lecomte, L.; Sinou, D.; Bakos, J.; Tóth, I.; Heil, B. J. Organomet. Chem. 1989, 370, 277-284. Laghmari, M.; Sinou, D. J. Mol. Catal. 1991, 66, L15-L18.