Process Research and Development of an Enantiomerically Enriched Allyic Amine, One of the Key Intermediates for the Manufacture of Synthetic Tetracyclines

Organic Process Research and Development

Volumn 19, Issue 11, 2015, Pages 1784-1795

  Zhang, Wu Yan ^a   Hogan, Philip C ^a   Chen, Chi Li ^a   Niu, John ^a   Wang, Zhimin ^a   Lafrance, Danny ^a   Gilicky, Olga ^a   Dunwoody, Nicholas ^a   Ronn, Magnus ^a  

^a Tetraphase Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; COST EFFECTIVENESS; ENANTIOMERS;

ALLYLIC AMINES; COST EFFECTIVE; DIMETHYL MALEATE; MANUFACTURING PROCESS; RESEARCH AND DEVELOPMENT;

MANUFACTURE;

EID: 84947908169     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/acs.oprd.5b00274     Document Type: Article

References (18)

1. Ronn, M.; Zhu, Z.; Hogan, P. C.; Zhang, W.-Y.; Niu, J.; Katz, C. E.; Dunwoody, N.; Gilicky, O.; Deng, Y.; Hunt, D. K.; He, M.; Chen, C.-L.; Sun, C.; Clark, R. B.; Xiao, X.-Y. Org. Process Res. Dev. 2013, 17, 838-845 10.1021/op4000219
2. Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R.; Myers, A. G. Science 2005, 308, 395 10.1126/science.1109755
3. Charest, M. G.; Siegel, D. R.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 8292 10.1021/ja052151d
4. Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P. M.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913 10.1021/ja806629e
5. Brubaker, J. D.; Myers, A. G. Org. Lett. 2007, 9, 3523 10.1021/ol071377d
6. Riess, R.; Schön, M.; Laschat, S.; Jäger, V. Eur. J. Org. Chem. 1998, 1998, 473 10.1002/(SICI)1099-0690(199803)1998:3<473::AID-EJOC473>3.0.CO;2-V
7. Bennouna, C.; Petrus, F.; Verducci, J. Bulletin de la Societe Chimique de France 1980, 9-10 (2) 478-80
8. Price, C. C.; Thorpe, R. S. J. Am. Chem. Soc. 1938, 60, 2839 10.1021/ja01279a003
9. Yu, S.; Ou, Z.; Li, S. Hunan Shifan Daxue Ziran Kexue Xuebao 1997, 20, 45
10. Ranu, B. C.; Jana, R. J. Org. Chem. 2005, 70, 8621 10.1021/jo051373r
11. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028 10.1021/ja00193a040
12. Oppolzer, W.; Radinov, R. Tetrahedron Lett. 1991, 32, 5777 10.1016/S0040-4039(00)93553-6
13. For a review, see: Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984 10.1021/ar020066u
14. Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron Lett. 2009, 50, 4188-4190 10.1016/j.tetlet.2009.05.008
15. Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron: Asymmetry 2008, 19, 2484-2491 10.1016/j.tetasy.2008.10.012
16. Hatano, M.; Ito, O.; Suzuki, S.; Ishihara, K. J. Org. Chem. 2010, 75, 5008-5016 10.1021/jo100563p
17. Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. Tetrahedron 2004, 60, 7899-7906 10.1016/j.tet.2004.06.045
18. Erickson, L. E. J. Am. Chem. Soc. 1965, 87, 1867 10.1021/ja01087a007