Application of P,N-Sulfinyl Imine Ligands to Iridium-Catalyzed Asymmetric Hydrogenation of Olefins

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 1800-1802

  Schenkel, Laurie B ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DATA REDUCTION; HYDROGENATION; IRIDIUM;

ENANTIOSELECTIVITIES; IMINE LIGANDS;

OLEFINS;

ALKENE DERIVATIVE; IMINE; IRIDIUM; LIGAND; P,N SULFINYLIMINE; PHOSPHINE; SULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ELECTRONICS; ENANTIOSELECTIVITY; HYDROGENATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKENES; AMIDES; CATALYSIS; HYDROGENATION; IMINES; IRIDIUM; LIGANDS; PHOSPHINES; STEREOISOMERISM; STILBENES; SULFONIUM COMPOUNDS;

EID: 1642391051     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035675+     Document Type: Article

References (29)

1. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
2. (a) Owens, T. D.; Hollander F.; Oliver, A.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539.
3. (b) Owens, T. D.; Souers, A. J.; Ellman, J. A. J. Org. Chem. 2003, 68, 3.
4. (c) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
5. (d) Souers, A. J.; Owens, T. D.; Ellman, J. A. Inorg. Chem. 2001, 40, 5299.
6. For leading references, phosphorus ligands, see: (a) Ohashi, A.; Kikuchi, S.-I.; Yasutake, M.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535.
7. (b) Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Kadyrov, R.; Fischer, C.; Börner, A. Tetrahedron: Asymmetry 2003, 14, 2739.
8. (c) Suárez, A.; Pizzano, A. Tetrahedron: Asymmetry 2001, 2501.
9. (d) Albert, J.; Cadena, J. M.; Granell, J.; Muller, G.; Ordinas, J.; Panyella, D.; Puerta, C.; Sañudo, C.; Valerga, P. Organometallics 1999, 18, 3511.
10. For sulfoximines, see: (a) Bolm, C.; Verrucci, M.; Simić, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2826.
11. (b) Bolm, C.; Simić, O. J. Am. Chem. Soc. 2001, 123, 3830.
12. (c) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321.
13. For sulfoxides, see: (a) Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
14. (a) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317.
15. (b) Liu, G.; Cogan, D.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
16. (a) Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880.
17. (b) Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Pflum, D. A.; Senanayake, C. H. Tetrahedron Lett. 2003, 44, 4195.
18. For leading references on related systems for Ir-catalyzed asymmetric hydrogenations, see: (a) Bunlaksananusorn, T.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 3941.
19. (b) Xu, G.; Gilbertson, S. R. Tetrahedron Lett. 2003, 44, 953.
20. (c) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391.
21. (d) Perry M. C.; Cui, X.; Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 113.
22. (e) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
23. Crabtree, R. Acc. Chem. Res. 1979, 12, 331.
24. (a) Menges, F.; Neuberger, M.; Pfaltz, A. Org. Lett. 2002, 4, 4713.
25. (b) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40.
26. (c) Blackmond, D. G.; Lightfoot, A.; Pfaltz, A.; Rosner, T.; Schnider, P.; Zimmerman, N. Chirality 2000, 12, 442.
27. (d) Cozzi, P. G.; Zimmerman, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450.
28. (e) Hilgraf, R.; Pfaltz, A. Synlett. 1999, 11, 1814.
29. (e) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897.