Chiral rhodium complexes containing bidentate ligands derived from (R,R)-1,2-diaminocyclohexane for catalytic enantioselective hydrosilylation of acetophenone

Journal of Molecular Catalysis A: Chemical

Volumn 222, Issue 1-2, 2004, Pages 47-52

  Arena, Carmela G ^a   Pattacini, Roberto ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Enantioselectivity; Hydrosilylation; N,P ligands; P ligands; Rhodium

Indexed keywords

BIDENTATE LIGANDS; CHEMICAL COMPLEXES; CHIRALS; PRECATALYSTS;

CATALYST ACTIVITY; CATALYSTS; MIXTURES; MONOMERS; POSITIVE IONS; SOLUTIONS; X RAY ANALYSIS;

RHODIUM COMPOUNDS;

1,2 DIAMINOCYCLOHEXANE; ACETOPHENONE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROSILYLATION; REACTION ANALYSIS;

EID: 5144219794     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.07.012     Document Type: Article

References (27)

1. H. Brunner M. Beller C. Bolm Transition Metals in Organic Synthesis 1998 Wiley-VCH Weinheim 131 140
2. H. Nishiyama E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin (Chapter 6.3)
3. Some recent examples:
4. D.K. Heldmann, and D. Seebach Helv. Chim. Acta 82 1999 1096 1110
5. R. Kuwano, M. Sawamura, J. Shirai, M. Takahashi, and Y. Ito Bull. Chem. Soc. Jpn. 73 2000 485 496
6. M. Diéguez, O. Pàmies, A. Ruiz, and C. Claver Tetrahedron: Asymmetry 13 2002 83 86
7. B. Tao, and G.C. Fu Angew. Chem. Int. Ed. 41 2002 3892 3894
8. K. Kromm, P.L. Osburn, and J.A. Gladysz Organometallics 21 2002 4275 4280
9. D.A. Evans, E.F. Michael, J.S. Tedrow, and K.R. Campos J. Am. Chem. Soc. 125 2003 3534 3543
10. W.L. Duan, M. Shi, and G.B. Rong Chem. Commun. 2003 2916 2917
11. S.P. Shum, S.D. Pastor, A.D. DeBellis, P.A. Odorisio, L. Burke, F.H. Clarke, G. Rihs, B. Piatek, and R.K. Rodebaugh Inorg. Chem. 42 2003 5097 5106
12. C.G. Arena, V. Casilli, and F. Faraone Tetrahedron: Asymmetry 14 2003 2127 2131
13. K. Onuma, T. Ito, and A. Nakamura Tetrahedron: Lett. 34 1979 3163 3166
14. SMART Software Users Guide, Version 5.0, Bruker Analytical X-ray Systems, Madison, WI, 1999; SAINT Software Users Guide, Bruker Analytical X-ray Systems, Madison, WI, 1999
15. SMART Software Users Guide, Version 5.0, Bruker Analytical X-ray Systems, Madison, WI, 1999; SAINT Software Users Guide, Bruker Analytical X-ray Systems, Madison, WI, 1999
16. G.M. Sheldrick SADABS 1999 Bruker Analytical X-ray Systems Madison, WI
17. G.M. Sheldrick SHELXL-93, A Program for Crystal Structure Determination 1993 University of Göttingen Germany
18. G.M. Sheldrick SHELXL-97, Program for Crystal Structure Refinement 1997 University of Göttingen Germany
19. P.R. Sharp E.W. Abel F.G.A. Stone G. Wikinson Comprehensive Organometallic Chemistry vol. 8 1995 Elsevier Science Ltd. Berlin
20. S.P. Shum, S.D. Pastor, and G. Rihs Inorg. Chem. 41 2002 127 131
21. Recently, an improved synthesis of 2 has been published see:
22. K.A. Rashid, A.J. Lough, and R.H. Morris Organometallics 20 2001 1047 1049
23. For other hydrosilylation catalysts which display unusual temperature dependence see:
24. Ref. [3e and f]
25. I. Ojima, T. Kogure, and M. Kumagai J. Org. Chem. 42 1977 1671 1679
26. There are only a few detailed mechanistic studies of rhodium catalyzed asymmetric hydrosilylation of ketones. See for example
27. D. Haag, J. Runsink, and H.-D. Scharf Organometallics 17 1998 398 409