Enantioselective synthesis of optically active alkanephosphonates via rhodium-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates with ferrocene-based monophosphoramidite ligands

Advanced Synthesis and Catalysis

Volumn 350, Issue 13, 2008, Pages 1979-1983

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

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Alkanephosphonates; Asymmetric catalysis; Hydrogenation; Monophosphoramidite ligands; Rhodium

Indexed keywords

EID: 53849139790     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800388     Document Type: Article

References (61)

1. a) R. L. Hilderbrand, The Role of Phosphonates in Living Systems, CRC Press, Boca Raton, 1983;
2. b) C. Bellucci, F. Gualtieri, S. Scapecchi, E. Teodori, R. Budriesi, A. Chiarini, Farmaco 1989, 44, 1167-1191;
3. c) P. Kafarski, B. Lejczak, Phosphorus Sulfur Relat. Elem. 1991, 63, 193-215;
4. d) K. W. Jung, K. D. Janda, P. J. Sanfilippo, M. Wachter, Bioorg. Med. Chem. Lett. 1996, 6, 2281-2282;
5. e) C.-H. L. Lo, P. Wentworth, K. W. Jung, J. Yoon, J. A. Ashley, K. D. Janda, J. Am. Chem. Soc. 1997, 119, 10251-10252;
6. f) A. Datta, P. Wentworth, J. P. Shaw, A. Simeonov, K. D. Janda, J. Am. Chem. Soc. 1999, 121, 10461-10467;
7. g) P. Kafarski, B. Lejczak, Curr. Med. Chem.-Anti-Cancer Agents 2001, 1, 301-312;
8. h) O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 2005, 16, 3295-3340.
9. a) S. E. Kelly, in: Comprehensive Organic Synthesis, Vol. 1, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp 761-773;
10. b) P. Savignac, B. Iorga, Morden Phosphonate Chemistry, CRC Press, Boca Raton, 2003.
11. a) J. Omelanzcuk, A. E. Sopchik, S.-G. Lee, K. Akutagawa, S. M. Cairns, W. G. Bentrude, J. Am. Chem. Soc. 1988, 110, 6908-6909;
12. b) S. M. Cairns, W. G. Bentrude, Tetrahedron Lett. 1989, 30, 1025-1028;
13. c) S. E. Denmark, C.-T. Chen, J. Am. Chem. Soc. 1995, 117, 11879-11897;
14. d) M. Kranz, S. E. Denmark, J. Org. Chem. 1995, 60, 5867-5877;
15. e) Y. L. Bennani, S. Hanessian, Tetrahedron 1996, 52, 13837-13866;
16. f) W. Bhanthumnavin, A. Arif, W. G. Bentrude, J. Org. Chem. 1998, 63, 7753-7758;
17. g) N. S. Goulioukina, T. M. Dolgina, I. P. Beletskaya, J.-C. Henry, D. Lavergne, V. Ratovelomanana-Vidal, J.-P. Genet, Tetrahedron: Asymmetry 2001, 12, 319-327;
18. h) N. S. Goulioukina, T. M. Dolgina, G. N. Bondarenko, I. P. Beletskaya, M. M. Ilyin, V. A. Davankov, A. Pfaltz, Tetrahedron: Asymmetry 2003, 14, 1397-1401.
19. T. Hayashi, T. Senda, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 1999, 121, 11591-11592.
20. a) D.-Y. Wang, X.-P. Hu, J.-D. Huang, J. Deng, S.-B. Yu, Z.-C. Duan, X.-F. Xu, Z. Zheng, Angew. Chem. Int. Ed. 2007, 46, 7810-7813;
21. b) D.-Y. Wang, J.-D. Huang, X.-P. Hu, J. Deng, S.-B. Yu, Z.-C. Duan, Z. Zheng, J. Org. Chem. 2008, 73, 2011-2014.
22. For reviews, see: a) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069;
23. b) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272-3296;
24. c) K. Källströn, I. Munslow, P. G. Andersson, Chem. Eur. J. 2006, 12, 3194-3200;
25. d) S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402-1411.
26. a) M. Kitamura, M. Tokunaga, T. Pham, W. D. Lubell, R. Noyori, Tetrahedron Lett. 1995, 36, 5769-5772;
27. b) M. Kitamura, M. Tokunaga, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2931-2932;
28. c) U. Schmidt, G. Oehme, H. Krause, Synth. Commun. 1996, 26, 777-781;
29. d) I. Grassert, U. Schmidt, S. Ziegler, C. Fischer, G. Oehme, Tetrahedron: Asymmetry 1998, 9, 4193-4202;
30. e) T. Dwars, U. Schmidt, C. Fischer, I. Grassert, R. Kempe, R. Fröhlich, K. Drauz, G. Oehme, Angew. Chem. Int. Ed. 1998, 37, 2851-2853;
31. f) J. Holz, M. Quirmbach, U. Schmidt, D. Heller, R. Stürmer, A. Börner, J. Org. Chem. 1998, 63, 8031-8034;
32. g) M. J. Burk, T. A. Stammers, J. A. Straub, Org. Lett. 1999, 1, 387-390;
33. h) I. D. Gridnev, N. Higashi, T. Imamoto, J. Am. Chem. Soc. 2001, 123, 4631-4632;
34. i) I. D. Gridnev, M. Yasutake, T. Imamoto, I. P. Beletskaya, Proc. Natl. Acad. Sci. USA 2004, 101, 5385-5390;
35. j) M. Rubio, A. Suárez, E. Álvarez, A. Pizzano, Chem. Commun. 2005, 628-630;
36. k) H. Liu, Y.-G. Zhou, Z.-K. Yu, W.-J. Xiao, S.-H. Liu, H.-W. He, Tetrahedron 2006, 62, 11207-11217;
37. l) M. Rubio, S. Vargas, A. Suárez, E. Álvarez, A. Pizzano, Chem. Eur. J. 2007, 13, 1821-1833;
38. m) R. Kadyrov, J. Holz, B. SchOffner, O. Zayas, J. Almena, A. Börner, Tetrahedron: Asymmetry 2008, 19, 1189-1192.
39. a) K. Achiwa, T. Soga, Tetrahedron Lett. 1978, 19, 1119-1120;
40. b) M. Furukawa, T. Okawara, Y. Noguchi, Y. Terawaki, Chem. Pharm. Bull. 1979, 27, 2223-2226;
41. c) W. D. Lubell, M. Kitamura, R. Noyori, Tetrahedron: Asymmetry 1991, 2, 543-554;
42. d) G. Zhu, Z. Chen, X. Zhang, J. Org. Chem. 1999, 64, 6907-6910;
43. e) M. Yasutake, I. D. Gridnev, N. Higashi, T. Imamoto, Org. Lett. 2001, 3, 1701-1704;
44. f) D. Heller, J. Holz, H. J. Drexler, J. Lang, K. Drauz, H.-P. Krimmer, A. Börner, J. Org. Chem. 2001, 66, 6816-6817;
45. g) Y.-G. Zhou, W. Tang, W.-B. Wang, W. Li, X. Zhang, J. Am. Chem. Soc. 2002, 124, 4952-4953;
46. h) W. Tang, X. Zhang, Org. Lett. 2002, 4, 4159-4161;
47. i) S.-G. Lee, Y. J. Zhang, Org. Lett. 2002, 4, 2429-2431;
48. j) D. Peña, A. J. Minnaard, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 14552-14553.
49. J. J. Kiddle, J. H. Babler , J. Org. Chem .1993, 58, 3572-3574.
50. a) Q.-B. Liu, C.-B. Yu, Y.-G. Zhou, Tetrahedron Lett. 2006, 47, 4733-4736;
51. b) Q.-B. Liu, Y.-G. Zhou, Tetrahedron Lett. 2007, 48, 2101-2104.
52. For a review, see: Y. Chi, W. Tang, X. Zhang, in: Modern Rhodium-Catalyzed Organic Reactions, (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, pp 1-31.
53. a) H. Huang, Z. Zheng, H. Luo, C. Bai, X. Hu, H. Chen, Org. Lett. 2003, 5, 4137-4139;
54. b) X.-P. Hu, Z. Zheng, Org. Lett. 2004, 6, 3585-3588;
55. c) H. Huang, Z. Zheng, H. Luo, C. Bai, X. Hu, H. Chen, J. Org. Chem. 2004, 69, 2355-2361;
56. d) X.-P. Hu, Z. Zheng, Org. Lett. 2005, 7, 419-422;
57. e) J.-D. Huang, X.-P. Hu, Z.-C. Duan, Q.-H. Zeng, S.-B. Yu, J. Deng, D.-Y. Wang, Z. Zheng, Org. Lett. 2006, 8, 4367-4370;
58. f) H. Huang, X. Liu, J. Deng, M. Qiu, Z. Zheng, Org. Lett. 2006, 8, 3359-3362;
59. g) J. Deng, Z.-C. Duan, J.-D. Huang, X.-P. Hu, D.-Y. Wang, S.-B. Yu, X.-F. Xu, Z. Zheng, Org. Lett. 2007, 9, 4825-4828;
60. h) J. Deng, X.-P. Hu, J.-D. Huang, S.-B. Yu, D.-Y. Wang, Z.-C. Duan, Z. Zheng, J. Org. Chem. 2008, 73, 2015-2017.
61. Q.-H. Zeng, X.-P. Hu, Z.-C. Duan, X.-M. Liang, Z. Zheng, J. Org. Chem. 2006, 71, 393-396.