New diphosphinite ligands derived from mannitol for rhodium catalyzed enantioselective hydrogenation of ketones

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2867-2870

  Naili, Said ^a   Suisse, Isabelle ^a   Mortreux, André ^a   Agbossou, Francine ^a   Ait Ali, Mustapha ^b   Karim, Abdallah ^b  

^a CNRS   (France)

^b FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

Author keywords

Diphosphanes; Enantioselective hydrogenation; Ketones; Rhodium

Indexed keywords

KETONE; MANNITOL; PHOSPHINE DERIVATIVE; RHODIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; HYDROGENATION; LIGAND BINDING;

EID: 0034655851     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00274-4     Document Type: Article

References (34)

1. (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993.
3. (c) Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, 1993; Vol. I and II.
4. Lead references to diphosphinite ligands.
5. (a) Hayashi, T.; Tanaka, M.; Ogata, I. Tetrahedron Lett. 1977, 3, 295-296.
6. (b) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62-65.
7. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 3133-3136.
8. (d) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C.-P. J. Am. Chem. Soc. 1997, 119, 9570-9571.
9. Examples of carbohydrate diphosphinites.
10. (a) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213-225 and references cited therein.
11. (b) Selke, R. ibid. 1986, 37, 227-234.
12. (c) Selke, R.; Schwarze, M.; Baudish, H.; Grassert, I.; Michalik, M.; Oehme, G.; Stoll, N.; Costisella, B. ibid. 1993, 84, 223-237.
13. (d) Selke, R. J. Organomet. Chem. 1989, 370, 241-248.
14. (e) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635-1636.
15. (f) Kreutzfeld, H.-J.; Döbler, C.; Krause, H. W.; Facklam, B. Tetrahedron: Asymmetry, 1993, 4, 2047-2051.
16. (g) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 62, 6012-6028.
17. (h) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429-3447.
18. For examples of open chain sugar based diphosphanes.
19. (a) Yamashita, M.; Naoi, M.; Imoto, H.; Oshikawa, T. Bull. Soc. Chem. Jpn. 1989, 62, 942-944.
20. (b) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960.
21. (c) Bendaya, A.; Masotti, H.; Peiffer, G.; Siv, C.; Archalvis, A. J. Organomet. Chem. 1993, 444, 41-46.
22. (d) Choudary, B. M.; Ravichandra Sarma, M.; Dyurga Prasad, A.; Narender, N. Indian J. Chem. 1994, 33B, 152-155.
23. (a) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 180, 1615-1645.
24. (a) Agbossou, F.; Carpentier, J.-F.; Hatat, C.; Kokel, N.; Mortreux, A.; Betz, P.; Goddard, R.; Krüger, C. Organometallics 1995, 14, 2480-2489.
25. (b) Roucoux, A.; Thieffry, L.; Carpentier, J.-F.; Devocelle, M.; Méliet, C.; Agbossou, F.; Mortreux, A. Organometallics 1996, 15, 2440-2449.
26. (c) Pasquier, C.; Naili, S.; Pelinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193-196.
27. (d) Devocelle, M.; Agbossou, F.; Mortreux, A. Synlett 1997, 1306-1308.
28. Baggett, N.; Striblehill, P. J. Chem. Soc., Perkin Trans. 1 1977, 1123-1126.
29. 31P NMR always assayed that the reactions went to completion over the course of 18 h at room temperature.
30. 2, δ ppm) 2, 116; 3, 142; 4, 146.
31. 2: Lahoz, F.; Martin, A.; Esteruelas, M. A.; Sola, E.; Serrano, J. L.; Oro, L. A. Organometallics 1991, 10, 1794-1799.
32. 2: Lahoz, F.; Martin, A.; Esteruelas, M. A.; Sola, E.; Serrano, J. L.; Oro, L. A. Organometallics 1991, 10, 1794-1799.
33. This behavior is following what is generally observed with AMPP ligands as well.
34. Such a trend has been observed twice with AMPP ligands, see: Roucoux, A.; Suisse, I.; Devocelle, M.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1996, 7, 379-382 and Ref. 6a.