Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: An approach to γ-amino acids

Tetrahedron Letters

Volumn 52, Issue 7, 2011, Pages 830-833

  Han, Fuzhong ^a,b,c   Chen, Jun ^a,b,c   Zhang, Xiangyang ^a,b,c   Liu, Jibing ^a,b,c   Cun, Linfeng ^a,b,c   Zhu, Jin ^a,b,c   Deng, Jingen ^a,b,c   Liao, Jian ^a,b,c  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Aminobutyric acids; 1,4 Addition; Bis sulfoxide ligand; Rh catalyzed

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; AMINO ACID; BACLOFEN; BORONIC ACID DERIVATIVE; ESTER; ETHYL GAMMA PHTHALIMIDOCROTONATE; LIGAND; RHODIUM; ROLIPRAM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY;

EID: 78651403377     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.044     Document Type: Article

References (39)

1. M. Bartók Chem. Rev. 110 2010 1663
2. N.G. Bowery, D.R. Hill, A.L. Hudson, A. Doble, N.D. Middemiss, J. Shaw, and M. Turnbull Nature 283 1980 92
3. R.B. Silverman, R. Andruszkiewicz, S.M. Nanavati, C.P. Taylor, and M.G. Vartanian J. Med. Chem. 34 1991 2295
4. G. Costantino, A. Macchiarulo, A.E. Guadix, and R. Pellicciari J. Med. Chem. 44 2001 1827
5. R.D. Allan, M.C. Bates, C.A. Drew, R.K. Duke, T.W. Hambley, G.A.R. Johnston, K.N. Mewett, and I. Spence Tetrahedron 46 1990 2511
6. T.R. Belliotti, T. Capiris, V. Ekhato, J.J. Kinsora, M.J. Field, T.G. Heffner, L.T. Melzer, J.B. Schwarz, C.P. Taylor, A.J. Thorpe, M.G. Vartanian, L.D. Wise, T. Zhi-Su, M.L. Weber, and D.J. Wustrow J. Med. Chem. 48 2005 2294
7. J. Ong, D.I.S. Kerr, D.J. Doolette, R.K. Duke, K.N. Mewett, R.D. Allen, and G.A.R. Johnston Eur. J. Pharmacol. 233 1993 169
8. M. Ordǒňez, and C. Cativiela Tetrahedron: Asymmetry 18 2007 3
9. P. Claudio, L. Aitor, M. Antonia, O. Mikel, P. Angel, and V. Silvia Angew. Chem., Int. Ed. 46 2007 8431
10. I. Kennosuke, and K. Shuji J. Am. Chem. Soc. 124 2002 13394
11. G. Hoge J. Am. Chem. Soc. 125 2003 10219
12. M.J. Burk, P.D. de Koning, T.M. Grote, M.S. Hoekstra, G. Hoge, R.A. Jennings, W.S. Kissel, T.V. Le, I.C. Lennon, T.A. Mulhern, J.A. Ramsden, and R.A. Wade J. Org. Chem. 68 2003 5731
13. G. Hoge, H.-P. Wu, W.S. Kissel, D.A. Pflum, D.J. Greene, and J. Bao J. Am. Chem. Soc. 126 2004 5966
14. A.S. Paraskar, and A. Sudalai Tetrahedron 62 2006 4907
15. J. Deng, Z.-C. Duan, J.-D. Huang, X.-P. Hu, D.-Y. Wang, S.-B. Yu, X.-F. Xu, and Z. Zheng Org. Lett. 9 2007 4825
16. J. Deng, X.-P. Hu, J.-D. Huang, S.-B. Yu, D.-Y. Wang, Z.-C. Duan, and Z. Zheng J. Org. Chem. 73 2008 6022
17. O. Meyer, J.-M. Becht, and G. Helmchen Synlett 2003 1539
18. J.-M. Becht, O. Meyer, and G. Helmchen Synthesis 2003 2805
19. Using chiral diphenylphosphino-functionalized NHC as ligand, see: J.-M. Becht, E. Bappert, and G. Helmchen Adv. Synth. Catal. 347 2005 495
20. Selected examples: S. Sakuma, M. Sakai, R. Itooka, and N. Miyaura J. Org. Chem. 65 2000 5951
21. T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829
22. T. Hayashi Pure Appl. Chem. 76 2004 465
23. E.M. Carreira, H. Grutzmacher, and C. Defieber Angew. Chem., Int. Ed. 47 2008 4482
24. T. Nishimura, J. Wang, M. Nagaosa, K. Okamoto, R. Shintani, F.Y. Kwong, W.Y. Yu, S.C.A. Chan, and T. Hayashi J. Am. Chem. Soc. 132 2010 464
25. H.J. Edwards, J.D. Hargrave, S.D. Penrose, and C.G. Frost Chem. Soc. Rev. 39 2010 2093
26. Selected examples: B.R. James, and R.S. McMillan Can. J. Chem. 55 1977 3927
27. N. Khiar, I. Fernandez, and F. Alcudia Tetrahedron Lett. 34 1993 123
28. R. Tokunoh, M. Sodeoka, K.-I. Aoe, and M. Shibasaki Tetrahedron Lett. 36 1995 8035
29. R. Mariz, X.J. Luan, M. Gatti, A. Linden, and R. Dorta J. Am. Chem. Soc. 130 2008 2172
30. J.J. Bürgi, R. Mariz, M. Gatti, E. Drinkel, X.J. Luan, S. Blumentritt, A. Linden, and R. Dorta Angew. Chem., Int. Ed. 48 2009 2768
31. J.-M. Chen, D. Li, H.F. Ma, L.-F. Cun, J. Zhu, J.-G. Deng, and J. Liao Tetrahedron Lett. 49 2008 6921
32. P. Wang, J.-M. Chen, L.F. Cun, J.-G. Deng, J. Zhu, and J. Liao Org. Biomol. Chem. 7 2009 3741
33. J.-M. Chen, F. Lang, D. Li, L.-F. Cun, J. Zhu, J.-G. Deng, and J. Lioa Tetrahedron: Asymmetry 2009 1953 20
34. J. Chen, J.-M. Chen, F. Lang, X.-Y. Zhang, L.F. Cun, J. Zhu, J.-G. Deng, and J. Liao J. Am. Chem. Soc. 132 2010 4552
35. F. Lang, D. Li, J.-M. Chen, J. Chen, L.C. Li, L.F. Cun, J. Zhu, J.-G. Deng, and J. Liao Adv. Synth. Catal. 352 2010 843
36. D. Todd, and S. Teich J. Am. Chem. Soc. 75 1953 1895
37. P.W. Baures, D.S. Eggleston, K.F. Erhard, L.B. Cieslinski, T.J. Torphy, and S.B. Christensen J. Med. Chem. 36 1993 3274
38. J. Mulzer J. Prakt. Chem. 336 1994 287
39. N. Sommer, P.A. Loeschmann, G.H. Northoff, M. Weller, A. Steinbrecher, J.P. Steinbach, R. Lichtenfiels, R. Meyermann, A. Reithmueller, A. Fontana, J. Dichgans, and R. Martin Nat. Med. 1 1995 244