Zinc-catalyzed aerobic oxidation of benzoins and its extension to enantioselective oxidation

Tetrahedron Letters

Volumn 52, Issue 6, 2011, Pages 692-695

  Muthupandi, Pandi ^a   Sekar, Govindasamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Aerobic oxidation; Enantioselective oxidation; Kinetic resolution; Molecular oxygen; Zinc catalyst

Indexed keywords

BENZOIN; OXYGEN; TOLUENE; ZINC; ZINC COMPLEX; ZINC OXIDE; ZINC SULFATE;

ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; OXIDATION; REACTION TIME; SYNTHESIS;

EID: 79251601341     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.004     Document Type: Article

References (34)

1. J. Tsuji Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis 2002 John Wiley and Sons New York
2. M. Beller, and C. Bolm Transition Metals for Organic Synthesis 2004 Wiley-VCH Weinheim
3. H. Yamamoto, and Lewis Acids in Organic Synthesis Wiley-VCH 2008 Weinheim
4. W.N. Lipscomb, and N. Straeter Chem. Rev. 96 1996 2375
5. J. Jankowska, J. Paradowska, B. Rakiel, and J. Mlynarski J. Org. Chem. 72 2007 2228
6. E.J. Corey, D.H. Lee, and S. Sarshar Tetrahedron: Asymmetry 6 1995 3
7. A. Ryoda, N. Yajima, T. Haga, T. Kumamoto, W. Nakanishi, M. Kawahata, K. Yamaguchi, and T. Ishikawa J. Org. Chem. 73 2008 133
8. L.R. Hillis, and R.C. Ronald J. Org. Chem. 50 1985 470
9. L. Janice, Hyatt, V. Stacy, R.M. Wadkins, K.J.P. Yoon, M. Wierdl, C.C. Edwards, M. Zeller, A.D. Hunter, M.K. Danks, G. Crundwell, and P.M. Potter J. Med. Chem. 48 2005 5543
10. B.I. Ita, and O.E. Offiong Mater. Chem. Phys. 70 2001 330
11. M.R. Ams, and C.S. Wilcox J. Am. Chem. Soc. 129 2007 3966
12. T. Kashiwabara, and M. Tanaka J. Org. Chem. 74 2009 3958
13. A. Giraud, O. Provot, Fran J., O. Peyrat, M. Alami, and J.D. Brion Tetrahedron 62 2006 7667
14. Y. Shimakawa, T. Morikawa, and S. Sakaguchi Tetrahedron Lett. 51 2010 1786
15. C. Joo, S. Kang, S.M. Kim, H. Han, and J.W. Yang Tetrahedron Lett. 51 2010 6006
16. J.M. Khurana, and B.M. Kandpal Tetrahedron Lett. 44 2003 4909 and references cited therein
17. T. Tanaka, M. Kawase, and S. Tani Bioorg. Med. Chem. 12 2004 501
18. O.B. Wallace, D.W. Smith, M.S. Deshpande, C. Polson, and K.M. Felsenstein Bioorg. Med. Chem. Lett. 13 2003 1203
19. Q.K. Fang, Z. Han, P. Grover, D. Kessler, C.H. Senanayake, and S.A. Wald Tetrahedron: Asymmetry 11 2000 3659
20. W. Adam, M. Lazarus, C.R. Saha-Moeller, and P. Schreier Acc. Chem. Res. 32 1999 837
21. F.A. Davis, and B.C. Chen Chem. Rev. 92 1992 919
22. For asymmetric benzoin condensations and enzymatic kinetic resolutions of racemic benzions: P.D. Dünkelmann, K.A. Nitsche, A.S. Demir, P. Siegert, L.B.M. Baumann, M. Pohl, and M. Müller J. Am. Chem. Soc. 124 2002 12084
23. D. Enders, O. Niemeier, and T. Balensiefer Angew. Chem., Int. Ed. 45 2006 1463
24. D. Enders, and U. Kallfass Angew. Chem., Int. Ed. 41 2002 1743
25. X. Linghu, and J.S. Johnson Angew. Chem., Int. Ed. 42 2003 2534
26. P. Hoyos, M. Fernndez, J.V. Sinisterra, and A.R. Alcntara J. Org. Chem. 71 2006 7632
27. S.K. Alamsetti, S. Mannam, P. Muthupandi, and G. Sekar Chem. Eur. J. 15 2009 1086
28. S.K. Alamsetti, P. Muthupandi, and G. Sekar Chem. Eur. J. 15 2009 5424
29. P. Muthupandi, S.K. Alamsetti, and G. Sekar Chem. Commun. 2009 3288
30. B.M. Trost Science 254 1991 1471
31. B.M. Trost Acc. Chem. Res. 35 2002 695
32. G. Parkin Chem. Rev. 104 2004 699
33. 1, 233.0578; found, 233.0585.
34. R (minor, 17.0 min).