Stereoselective synthesis of β-substituted β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines

Organic Letters

Volumn 8, Issue 4, 2006, Pages 789-792

  Velázquez, Francisco ^a   Arasappan, Ashok ^a   Chen, Kevin ^a   Sannigrahi, Mousumi ^a   Venkatraman, Srikanth ^a   McPhail, Andrew T ^a,b   Chan, Tze Ming ^a   Shih, Neng Yang ^a   Njoroge, F George ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644785717     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053132b     Document Type: Article

References (24)

1. Tamamura, H.; Koh, Y.; Ueda, S.; Sasaki, Y.; Yamasaki, T.; Aoki, M.; Maeda, K.; Watai, Y.; Arikuni, H.; Otaka, A.; Mitsuya, H.; Fujii, N. J. Med. Chem. 2003, 46, 1768.
2. Becker, D. P.; Barta, T. E.; Bedell, L.; DeCrescenzo, G.; Freskos, J.; Getman, D. P.; Hockerman, S. L.; Li, M.; Mehta, P.; Mischke, B.; Munie, G. E.; Swearingen, C.; Villamil, C. I. Bioorg. Med. Chem. Lett. 2001, 11, 2719.
3. McIntyre, J. A.; Castaner, J. Drugs Future 2004, 29, 985.
4. Lehman de Gaeta, L. S.; Czarniecki, M. J. Org. Chem. 1989, 54, 4004.
5. (a) Wada, C. K.; Holms, J. H.; Curtin, M. L.; Dai, Y.; Florjancic, A. S.; Garland, R. B.; Guo, Y.; Heyman, H. R.; Stacey, J. R.; Steinman, D. H.; Albert, D. H.; Bouska, J. J.; Elmore, I. N.; Goodfellow, C. L.; Marcotte, P. A.; Tapang, P.; Morgan, D. W.; Michaelides, M. R.; Davidsen, S. K. J. Med. Chem. 2002, 45, 219.
6. (b) Yamaguchi, M.; Nakao, H.; Goto, M.; Morimoto, M.; Fujioka, S.; Tohnishi, M. PCT Int. Appl. WO 2004018415, 2004.
7. (c) Burrows, J. N.; Tucker, H. PCT Int. Appl. WO 2004006925, 2004.
8. (a) Naimi-Jamal, M. R.; Ipaktschi, J.; Saidi, M. R. Eur. J. Org. Chem. 2000, 1735.
9. (b) Mladenova, M. Synth. Commun. 1986, 16, 1089.
10. (a) Enders, D.; Müller, S. F.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2000, 879.
11. (b) Enders, D.; Müller, S. F.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 195.
12. Ma, D.; Zhu, B.; Xu, H. Tetrahedron Lett. 2002, 43, 8511.
13. For recent reviews on the chemistry of N-sulfinyl imines see: (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
14. (b) Zhou, P.; Chen, B.; Davis, F. A. Tetrahedron 2004, 60, 8003.
15. One example on the addition of lithiated sulfones to chiral N-sulfinyl imines has been reported: Balasubramanian, T.; Hassner, A. Tetrahedron: Asymmetry 1998, 9, 2201.
16. (a) García Ruano, J. L.; Alcudia, A.; del Prado, M.; Barros, D.; Maestro, M. C.; Fernández, I. J. Org. Chem. 2000, 65, 2856.
17. (b) García Ruano, J. L.; Alemán, J.; Parra, A. J. Am. Chem. Soc. 2005, 127, 13048.
18. Li, Y.; Hu, J. Angew. Chem., Int. Ed. 2005, 44, 5882.
19. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
20. See the Supporting Information for detailed experimental procedures for addition reactions and synthesis of imines and sulfones.
21. Single-crystal X-ray analysis was performed for β-amino sulfone 16 and the configuration of the rest of the addition products was assigned by analogy based on the proposed transition state.
22. A number of addition products were N-deprotected under acidic conditions. The N-sulfinyl group was readily cleaved by treatment of methanolic solutions of addition products with 4 M HCl in dioxanes to give the corresponding amine hydrochloride salts.
23. (a) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
24. (b) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 1, 2056.