Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation

Tetrahedron Asymmetry

Volumn 22, Issue 24, 2011, Pages 2117-2123

  Luo, Li Bin ^a   Wang, Dao Yong ^b   Zhou, Xiao Mao ^a   Zheng, Zhuo ^a,b   Hu, Xiang Ping ^b  

^a HUNAN AGRICULTURAL UNIVERSITY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; FERROCENE DERIVATIVE; LIGAND; PHOSPHONIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIONIC ACID DERIVATIVE; RHODIUM;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84863010998     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.12.002     Document Type: Article

References (29)

1. P.A. Bartlett, and W.B. Kezer J. Am. Chem. Soc. 106 1984 4282
2. A.E. McDermott, F. Creuzet, R.G. Griffin, L.E. Zawadzke, Q.-Z. Ye, and C.T. Walsh Biochemistry 29 1990 5767
3. J. Hiratake, H. Kato, and J. Oda J. Am. Chem. Soc. 116 1994 12059
4. J.R. Morphy, N.R.A. Beeley, B.A. Boyce, J. Leonard, B. Mason, A. Millican, K. Millar, J.P. O'Connell, and J. Porter Bioorg. Med. Chem. Lett. 4 1994 2747
5. S. Vassiliou, A. Mucha, P. Cuniasse, D. Georgiadis, K. Lucet-Levannier, F. Beau, R. Kannan, G. Murphy, V. Knauper, M.-C. Rio, P. Basset, A. Yiotakis, and V. Dive J. Med. Chem. 42 1999 2610
6. N. Valiaeva, D. Bartley, T. Konno, and J.K. Coward J. Org. Chem. 66 2001 5146
7. H. Chen, F. Noble, B.P. Roques, and M.-C. Fournié-Zaluski J. Med. Chem. 44 2001 3523
8. P.F. Jackson, K.L. Tays, K.M. Maclin, Y.-S. Ko, W. Li, D. Vitharana, T. Tsukamoto, D. Stoermer, X.-C.M. Lu, K. Wozniak, and B.S. Slusher J. Med. Chem. 44 2001 4170
9. L. Demange, and C. Dugave Tetrahedron Lett. 42 2001 6295
10. M. Matziari, F. Beau, P. Cuniasse, V. Dive, and A. Yiptakis J. Med. Chem. 47 2004 325
11. D. Bartley, and J.K. Coward J. Org. Chem. 70 2005 6757
12. P. Majer, B. Hin, D. Stoermer, J. Adams, W. Xu, B.R. Duvall, G. Delahanty, Q. Liu, M.J. Stathis, K.M. Wozniak, B.S. Slusher, and T. Tsukamoto J. Med. Chem. 49 2006 2876
13. H. Chen, F. Noble, A. Mothé, H. Meudal, P. Coric, S. Danascimento, B.P. Roques, P. George, and M.C. Fournié-Zaluski J. Med. Chem. 43 2000 1398
14. X. Liu, E. Hu, X. Tian, A. Mazur, and F. Ebetino J. Organomet. Chem. 646 2002 212
15. M. Matziari, and A. Yiotakis Org. Lett. 7 2005 4049
16. For reviews, see: G. De Vries Handbook of Homogeneous Hydrogenation 2007 Wiley Weinheim
17. G. Shang, W. Li, and X. Zhang Catalytic Asymmetric Synthesis Third ed. 2010 Wiley Hoboken 343 436
18. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
19. H.U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103
20. Examples of the hydrogenation of β-substituted itaconates, see: M.J. Burk, F. Bienewald, M. Harris, and A. Zanotti-Gerosa Angew. Chem., Int. Ed. 37 1998 1931
21. J. Almena, A. Monsees, R. Kadyrov, T.H. Riermeier, B. Gotov, J. Holz, and A. Borner Adv. Synth. Catal. 346 2004 1263
22. W. Tang, D. Liu, and X. Zhang Org. Lett. 5 2003 205
23. D. Liu, and X. Zhang Eur. J. Org. Chem. 2005 646
24. P.A. Badkar, N.P. Rath, and C.D. Spilling Org. Lett. 9 2007 3619
25. D.-Y. Wang, X.-P. Hu, C.-J. Hou, J. Deng, S.-B. Yu, Z.-C. Duan, J.-D. Huang, and Z. Zheng Org. Lett. 11 2009 3226
26. T. Janecki, and R. Bodalski Synthesis 1990 799
27. H.G. McFadden, R.L.N. Harris, and C.L.D.A. Jenkins Aust. J. Chem. 42 1989 301
28. W.R. Schoen, and W.H. Parsons Tetrahedron Lett. 29 1988 5201
29. H. Mrabet, and H. Zantour Phosphorus, Sulfur Silicon Relat. Elem. 179 2004 25