Enantioselective synthesis of chiral α-aryl or α-alkyl substituted ethylphosphonates via Rh-catalyzed asymmetric hydrogenation with a P-stereogenic BoPhoz-type ligand

Journal of Organic Chemistry

Volumn 74, Issue 11, 2009, Pages 4408-4410

  Wang, Dao Yong ^a,b   Hu, Xiang Ping ^a   Deng, Jun ^a,b   Yu, Sai Bo ^a,b   Duan, Zheng Chao ^a,b   Zheng, Zhuo ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC HYDROGENATION; CHEMICAL EQUATIONS; ENANTIOSELECTIVE SYNTHESIS; OPTICALLY ACTIVE;

ALKYLATION; HYDROGENATION; LIGANDS; RHODIUM; SYNTHESIS (CHEMICAL);

CHELATION;

ETHYLPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS;

CATALYSIS; HYDROGENATION; LIGANDS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; RHODIUM; STEREOISOMERISM;

EID: 66249092771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900417m     Document Type: Article

References (41)

1. Engel, R. Chem. Rev. 1977, 77, 349-367.
2. (b) Marseigne, I.; Roques, B. P. J. Org. Chem. 1988, 53, 3621-3624.
3. (c) Bellucci, C.; Gualtieri, F.; Scapecchi, S.; Teodori, E.; Budriesi, R.; Chiarini, A. Farmaco 1989, 44, 1167-1191.
4. (d) Bigge, C. F.; Drummond, J. T.; Johnson, G.; Malone, T.; Probert, A. W.; Marcoux, F. W.; Coughenour, L. L.; Brahce, L. J. J. Med. Chem. 1989, 32, 1580-1590.
5. (e) Bigge, C. F.; Johnson, G.; Ortwine, D. F.; Drummond, J. T.; Retz, D. M.; Brahce, L. J.; Coughenour, L. L.; Marcoux, F. W.; Probert, A. W. J. Med. Chem. 1992, 35, 1371-1384.
6. (f) Liu, W.-Q.; Carreaux, F.; Meudal, H.; Roques, B. P.; Garbay-Jaureguiberry, C. Tetrahedron 1996, 52, 4411-4422.
7. (g) Lo, C.-H. L.; Wentworth, P.; Jung, K. W.; Yoon, J.; Ashley, J. A.; Janda, K. D. J. Am. Chem. Soc. 1997, 119, 10251-10252.
8. (h) Datta, A.; Wentworth, P.; Shaw, J. P.; Simeonov, A.; Janda, K. D. J. Am. Chem. Soc. 1999, 121, 10461-10467.
9. Jung, K. W.; Janda, K. D.; Sanfilippo, P. J.; Wachter, M. Bioorg. Med. Chem. Lett. 1996, 6, 2281-2282.
10. Bennani, Y. L.; Hanessian, S. Tetrahedron 1996, 52, 13837-13866.
11. (b) Kranz, M.; Denmark, S. E. J. Org. Chem. 1995, 60, 5867-5877.
12. (c) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
13. Cairns, S. M.; Bentrude, W. G. Tetrahedron Lett. 1989, 30, 1025-1028.
14. (b) Omelanzcuk, J.; Sopchik, A. E.; Lee, S.-G.; Akutagawa, K.; Cairns, S. M.; Bentrude, W. G. J. Am. Chem. Soc. 1988, 110, 6908-6909.
15. (c) Bhanthumnavin, W.; Arif, A.; Bentrude, W. G. J. Org. Chem. 1998, 63, 7753-7758.
16. For a review, see Church, T. L.; Andersson, P. G. Coord. Chem. Rev. 2008, 252, 513-531.
17. Henry, J.-C.; Lavergne, D.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Beletskaya, I. P.; Dolgina, T. M. Tetrahedron Lett. 1998, 39, 3473-3476.
18. (b) Goulioukina, N. S.; Dolgina, T. M.; Beletskaya, I. P.; Henry, J.-C.; Lavergne, D.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron: Asymmetry 2001, 12, 319-327.
19. Goulioukina, N. S.; Dolgina, T. M.; Bondarenko, G. N.; Beletskaya, I. P.; Ilyin, M. M.; Davankov, V. A.; Pfaltz, A. Tetrahedron: Asymmetry 2003, 14, 1397-1401.
20. Deng, J.; Duan, Z.-C.; Huang, J.-D.; Hu, X.-P.; Wang, D.-Y.; Yu, S.-B.; Xu, X.-F.; Zheng, Z. Org. Lett. 2007, 9, 4825-4828.
21. (b) Wang, D.-Y.; Huang, J.-D.; Hu, X.-P.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 2011-2014.
22. (c) Deng, J.; Hu, X.-P.; Huang, J.-D.; Yu, S.-B.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 2015-2017.
23. (d) Qiu, M.; Hu, X.-P.; Huang, J.-D.; Wang, D.-Y.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. Adv. Synth. Catal. 2008, 350, 2683-2689.
24. Boaz, N. W.; Debenham, S. D.; Mackenzie, E. B.; Large, S. E. Org. Lett. 2002, 4, 2421-2424.
25. (b) Boaz, N. W.; Large, S. E.; Ponasik, J. A., Jr.; Moore, M. K.; Barnette, T.; Nottingham, W. D. Org. Process Res. Dev. 2005, 9, 472-478.
26. (c) Boaz, N. W.; Ponasik, J. A., Jr.; Large, S. E. Tetrahedron: Asymmetry 2005, 16, 2063-2066.
27. (d) Li, X.; Jia, X.; Xu, L.; Kok, S. H. L.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1904-1908.
28. (e) Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.; Ponasik, J. A., Jr. J. Org. Chem. 2005, 70, 1872-1880.
29. (f) Boaz, N. W.; Ponasik, J. A., Jr.; Large, S. E. Tetrahedron Lett. 2006, 47, 4033-4035.
30. (g) Chen, W.; Mbafor, W.; Roberts, S. M.; Whittall, J. J. Am. Chem. Soc. 2006, 128, 3922-3923.
31. (h) Zanotti-Gerosa, A.; Kinney, W. A.; Grasa, G. A.; Medlock, J.; Seger, A.; Ghosh, S.; Teleha, C. A.; Maryanoff, B. E. Tetrahedron: Asymmetry 2008, 19, 938-944.
32. (i) Amoroso, D.; Graham, T. W.; Guo, R.; Tsang, C.-W.; Abdur-Rashid, K. Aldrichimica Acta 2008, 41, 15-26.
33. Cheruku, P.; Diesen, J.; Ahdersson, P. G. J. Am. Chem. Soc. 2008, 130, 5595-5599.
34. Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445-1446.
35. (b) Horner, L.; Siegel, H.; Büthe, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 942.
36. Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372.
37. Noyori, R. Acc. Chem. Res. 1990, 23, 345-350.
38. Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212-3215.
39. Hu, X.-P.; Zheng, Z. Org. Lett. 2004, 6, 3585-3588.
40. Huang, J.-D.; Hu, X.-P.; Duan, Z.-C.; Zeng, Q.-H.; Yu, S.-B.; Deng, J.; Wang, D.-Y.; Zheng, Z. Org. Lett. 2006, 8, 4367-4370.
41. Krueger, W. E.; Mclean, M. B.; Rizwaniuk, A.; Maloney, J. R.; Behelfer, G. L.; Boland, B. E. J. Org. Chem. 1978, 43, 2877-2879.