Rh-catalyzed asymmetric hydrogenation of α-aryl imino esters: An efficient enantioselective synthesis of aryl glycine derivatives

Angewandte Chemie - International Edition

Volumn 45, Issue 38, 2006, Pages 6360-6362

  Shang, Gao ^a   Yang, Qin ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Amino acids; Asymmetric catalysis; Enantioselectivity; Hydrogenation; Reduction

Indexed keywords

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY;

CATALYSIS; DERIVATIVES; HYDROGENATION; RHODIUM; SYNTHESIS (CHEMICAL);

ESTERS;

DRUG DERIVATIVE; ESTER; GLYCINE; IMINO ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GLYCINE; HYDROGENATION; IMINO ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 33749244636     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601540     Document Type: Article

References (33)

1. E. M. Meyer, W. H. J. Boesten, H. E. Schoemaker, J. A. M. van Balken in Biocatalysis in Organic Synthesis (Eds.: J. Tramper, H. C. van der Plas, P. Linko), Elsevier, Amsterdam, 1985, pp. 135-158.
2. C. A. Townsend, A. M. Brown, J. Am. Chem. Soc. 1983, 105, 913-918.
3. J. L. Spencer, E. H. Flynn, R. W. Roeske, F. Y. Siu, R. R. Chauvette, J. Med. Chem. 1966, 9, 746-750.
4. A. V. Rama Rao, M. K. Gurjar, K. Laxma Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2167.
5. a) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917, and references therein;
6. b) K. L. Reddy, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 1207-1217;
7. c) D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452-6453, and references therein;
8. d) M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910-4911;
9. e) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285;
10. f) J. M. Vernier, L. S. Hegedus, D. B. Miller, J. Org. Chem. 1992, 57, 6914-6920;
11. g) D. L. Boger, R. M. Borzilleri, S. Nukui, J. Org. Chem. 1996, 61, 3561-3565;
12. h) H. Kunz, W. Sager, Angew. Chem. 1987, 99, 595-597;
13. Angew. Chem. Int. Ed. Engl. 1987, 26, 557-559;
14. i) M. J. O'Donnell, W. D. Bennett, Tetrahedron 1988, 44, 5389-5401;
15. j) K. C. Nicolaou, H. J. Mitchell, N. F. Jain, N. Winssinger, R. Hughes, T. Bando, Angew. Chem. 1999, 111, 253-255;
16. Angew. Chem. Int. Ed. 1999, 38, 240-244.
17. a) P. A. Chaloner, M. A. Esteruelas, F. Joó, L. A. Oro, Homogeneous Hydrogenation, Kluwer, Dordrecht, 1994;
18. b) J. M. Brown, In Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 5.1;
19. c) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994, chap. 2;
20. d) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3070.
21. For reviews, see: a) F. Spindler, H.-U. Blaser in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 113-123;
22. b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094;
23. c) R. Kadyrov, T. H. Riermeier, U. Dingerdissen, V. Tararov, A. Börner, J. Org. Chem. 2003, 68, 4067-4070;
24. d) H. Abe, H. Amii, K. Uneyama, Org. Lett. 2001, 3, 313-315;
25. e) M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266-6267.
26. Y. Niwa, M. Shimizu, J. Am. Chem. Soc. 2003, 125, 3720-3721.
27. a) F. Palacios, D. Aparicio, J. García, E. Rodríguez, Eur. J. Org. Chem. 1998, 1413-1423;
28. b) D. Taniyama, M. Hasegawa, K. Tomioka, Tetrahedron Lett. 2000, 41, 5533-5536.
29. a) W. Tang, X. Zhang, Angew. Chem. 2002, 114, 1682-1684;
30. Angew. Chem. Int. Ed. 2002, 41, 1612-1614;
31. b) Q. Dai, W. Yang, X. Zhang, Org. Lett. 2005, 7, 5343-5345;
32. c) Q. Yang, W. Gao, J. Deng, X. Zhang, Tetrahedron Lett. 2006, 47, 821-823.
33. See supporting information for more results and experimental details.