Enantioselective hydrogenations of arylalkenes mediated by [Ir(cod)(JM-phos)]+ complexes

Chemistry - A European Journal

Volumn 7, Issue 24, 2001, Pages 5391-5400

  Hou, Duen Ren ^a   Reibenspies, Joseph ^a   Colacot, Thomas J ^b   Burgess, Kevin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b Johnson Matthey   (United States)

Author keywords

Alkenes; Asymmetric catalysis; Homogeneous catalysis; Hydrogenation; N ligands; P ligands

Indexed keywords

IRIDIUM COMPOUNDS; OLEFINS; PHOSPHORUS COMPOUNDS; SUBSTRATES; X RAY DIFFRACTION;

SQUARE PLANER METAL ENVIRONMENTS;

HYDROGENATION;

ALKENE DERIVATIVE; DEUTERIUM; IRIDIUM COMPLEX; OXAZOLINE DERIVATIVE; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COVALENT BOND; ENANTIOMER; HYDROGENATION; ISOTOPE LABELING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0035905355     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011217)7:24<5391::AID-CHEM5391>3.0.CO;2-1     Document Type: Article

References (37)

1. R. K. Halterman, K. P. C. Vollhardt, M. E. Welker, J. Am. Chem. Soc. 1987, 109, 8105-8107.
2. R. L. Halterman, K. P. C. Vollhardt, Organometallics 1988, 7, 883-892.
3. F. R. W. P. Wild, J. Zsolnai, G. Huttner, H. H. Brintzinger, J. Organomet. Chem. 1982, 232, 233-247.
4. R. Waymouth, P. Pino, J. Am. Chem. Soc. 1990, 112, 4911-4914.
5. R. B. Grossman, R. A. Doyle, S. L. Buchwald, Organometallics 1991, 10, 1501-1505.
6. R. D. Broene, S. L. Buchwald, J. Am. Chem. Soc. 1993, 115, 12569-12570.
7. M. V. Troutman, D. H. Appella, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4916-4917.
8. R. H. Crabtree, G. E. Morris, J. Organomet. Chem. 1977, 135, 395-403.
9. R. Crabtree, Acc. Chem. Res. 1979, 12, 331-337.
10. R. H. Crabtree, R. J. Uriarte, Inorg. Chem. 1983, 22, 4152-4154.
11. R. H. Crabtree, P. C. Demou, D. Eden, J. M. Mihelcic, C. A. Parnell, J. M. Quirk, G. E. Morris, J. Am. Chem. Soc. 1982, 104, 6994-7001.
12. A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. 1998, 110, 3047-3050;
13. Angew. Chem. Int. Ed. 1998, 37, 2897-2899.
14. D. G. Blackmond, A. Lightfoot, A. Pfaltz, T. Rosner, P. Schnider, N. Zimmermann, Chirality 2000, 12, 442-449.
15. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345.
16. D.-R. Hou, K. Burgess, Org. Lett. 1999, 1, 1745-1747.
17. D.-R. Hou, J. Reibenspies, K. Burgess, J. Org. Chem. 2001, 66, 206-215.
18. J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590.
19. N. Hishida, N. Takada, M. Yoshimura, T. Sonoda, H. Kobayashi, Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604.
20. M. Brookhart, B. Grant, A. F. Volpe, Organometallics 1992, 11, 3920-3922.
21. R. H. Crabtree, M. W. Davis, J. Org. Chem. 1986, 51, 2655-2661.
22. R. Kuwano, K. Sato, T. Kurokawa, D. Karube, Y. Ito, J. Am. Chem. Soc. 2000, 122, 7614-7615.
23. W. Chen, L. Xu, C. Chatterton, J. Xiao, Chem. Commun. 1999, 1247-1248.
24. J. H. Davis Jr., K. J. Forrester, Tetrahedron Lett. 1999, 40, 1621-1622.
25. C. W. Lee, Tetrahedron Lett. 1999, 40, 2461-2464.
26. L. Green, I. Hemeon, R. D. Singer, Tetrahedron Lett. 2000, 41, 1343-1346.
27. L. Xu, W. Chen, J. Xiao, Organometallics 2000, 19, 1123-1127.
28. C. E. Song, E. J. Roh, Chem. Commun. 2000, 837-838.
29. R. Hilgraf, A. Pfaltz, Synlelt 1999, 1814-1816.
30. Y. Sun, C. LeBlond, J. Wang, D. G. Blackmond, J. Am. Chem. Soc. 1995, 117, 12647-12648.
31. Y. Sun, J. Wang, C. LeBlond, R. A. Reamer, J. Laquidara, J. R. Sowa-Jr., D. G. Blackmond, J. Organomet. Chem. 1997, 548, 65-72.
32. J. M. Brown, A. E. Derome, G. D. Hughes, P. K. Monaghan, Aust. J. Chem. 1992, 45, 143-153.
33. H. Rottendorf, S. Sternhell, J. R. Wilmshurst, Aust. J. Chem. 1965, 18, 1759-1773.
34. A. P. Uijttewaal, F. L. Jonkers, A. v. d. Gen, J. Org. Chem. 1978, 43, 3306-3311.
35. A. Shitangkoon, G. Vigh, J. Chromatography A 1996, 738, 31-42.
36. L. A. Paquette, M. R. Sivik, E. I. Bzowej, K. J. Stanton, Organometallics 1995, 14, 4865-4878.
37. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-166174 (2j), -166175 (2b), -166176 (2i), and -166177 (2h). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).