An efficient enantioselective synthesis of florfenicol via asymmetric aziridination

Tetrahedron

Volumn 67, Issue 47, 2011, Pages 9199-9203

  Wang, Zhonghua ^a   Li, Feng ^a   Zhao, Lei ^a   He, Qiuqin ^a   Chen, Fener ^a   Zheng, Chen ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Asymmetric aziridination; Aziridine; Florfenicol; Middleton fluorination; VANOL

Indexed keywords

AZIRIDINE DERIVATIVE; ETHYL 1 BENZHYDRYL 3 [4 (METHYLSULFONYL)PHENYL]AZIRIDINE 2 CARBOXYLATE; FLORFENICOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC AZIRIDINATION; ASYMMETRIC SYNTHESIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RING OPENING;

EID: 80054736597     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.052     Document Type: Article

References (25)

1. Nagabhushan, T. L. U.S. Patent 4,235,892, 1980
2. Chem. Abstr. 96 1982 180950
3. D.P. Schumacher, J.E. Clark, B.L. Murphy, and P.A. Fischer J. Org. Chem. 55 1990 5291 5294
4. C. Giordano, S. Cavicchioli, S. Levi, and M. Villa J. Org. Chem. 56 1991 6114 6118
5. J.E. Clark, P.A. Fischer, and D.P. Schumacher Synthesis 10 1991 891 894
6. Wu, G.-Z.; Tormos, W. I. U.S. Patent 5,352,832, 1994
7. Chem. Abstr. 121 1994 133722
8. G.-Z. Wu, D.P. Schumacher, W. Tormos, E.J. Clark, and B.L. Murphy J. Org. Chem. 62 1997 2996 2998
9. W. Lu, P. Chen, and G. Lin Tetrahedron 64 2008 7822 7827
10. Tobiki, H.; Okamoto, T.; Akiyama, H. U.S. Patent 3,927,054, 1975
11. Chem. Abstr. 84 1976 165193
12. For the most recent reviews of the asymmetric aziridination
13. H. Pellissier Tetrahedron 66 2010 1509 1555
14. H. Muchalski, and J.N. Johnston Sci. Synth. Stereosel. Synth. 1 2011 155 184
15. F.A. Davis, and P. Zhou Tetrahedron Lett. 35 1994 7525 7528
16. C. Loncaric, and W.D. Wulff Org. Lett. 3 2001 3675 3678
17. Y. Zhang, Z. Lu, and W.D. Wulff Synlett 2009 2715 2739
18. L. Huang, and W.D. Wulff J. Am. Chem. Soc. 133 2011 8892 8895
19. CCDC-830153 contains the supplementary crystallographic data for (2S,3S)-aziridine 11. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
20. W.J. Middleton J. Org. Chem. 40 1975 574 578
21. For 7: D. Saelinger, and R. Brueckner Chem. - Eur. J. 15 2009 6688 6703
22. For 8: Inanaga, J. Eur. Pat. Appl. 1134209, 2001
23. Chem. Abstr. 135 2001 257051
24. For 9: R.I. Storer, D.E. Carrera, Y. Ni, and D.W.C. MacMillan J. Am. Chem. Soc. 128 2006 84 86
25. For 10: E. Weber, N. Doerpinghaus, and I. Goldberg J. Chem. Soc., Chem. Commun. 1988 1566 1568