A diastereoselective silver(I) promoted Gem-dibromocyclopropane ring opening reaction via an anchimeric assisted transannular benzoate migration

Heterocycles

Volumn 67, Issue 2, 2006, Pages 721-730

  Mortensen, Matt S ^a   Schmitt, Aaron C ^a   Smith, Catherine M ^a   Voight, Eric A ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646863236     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)69     Document Type: Article

References (16)

1. Carroll F., Lewin A., Boja J., and Kuhar M. J. Med. Chem. 35 (1992) 969
2. Carroll F., Kotian P., Dehghani A., Gray J., Kuzemko M., Parhan K., Abraham P., Lewin A., Boja J., and Kuhar M. J. Med. Chem. 38 (1995) 379
3. Meltzer P., Liang A., and Madras B. J. Med. Chem. 37 (1994) 2001
4. Newman A., Allen A., Izenwasser S., and Katz J. J. Med. Chem. 37 (1994) 2258
5. For the synthesis of 6- and 7-methoxy cocaine see. Simoni D., Roberti M., Andrisano V., Manferdini M., Rondanin R., and Kozikowski A. J. Org. Chem. 63 (1998) 4834
6. Simoni D., Stoelwinder J., Kozikowski A., Johnson K., Bergmann J., and Ball R. J. Med. Chem. 36 (1993) 3975
7. Zhao L., Johnson K., Zhang M., Flippen-Anderson K., and Kozikowski A. J. Med. Chem. 43 (2000) 3283
8. For a recent desymmetrization approach to cocaine see. Lee J., Lee K., and Cha J. J. Org. Chem. 65 (2000) 4773
9. For a review of dihalocyclopropane ring opening reactions, see. Banwell M., and Reum M. In: Halton B. (Ed). Advances In Strain In Organic Chemistry Vol. 1 (1991), Jai Press, Inc., Greenwich, CT
10. Li G., Chang H.-T., and Sharpless K.B. Angew. Chem., Int. Ed. Engl. 35 (1996) 451
11. Li G., Angert H., and Sharpless K. Angew. Chem., Int. Ed. Engl. 35 (1996) 2813
12. Schmitt A., Smith C., Voight E., and O'Doherty G. Heterocycles 62 (2004) 635
13. For Lewis acid catalyzed opening of aziridines see. Prasad B., Sekar G., and Singh V. and references therein. Tetrahedron Lett. 41 (2000) 4677
14. We have found that freshly prepared tetrabutylammonium perbromide provided similarly good yields of 5 and 8.
15. and ref. 10. Paquette L.A., Fristad W.E., Schuman C.A., Beno M.A., and Christoph C.G. J. Am. Chem. Soc. 101 (1979) 4645
16. Compounds (8, 9, 10, 12, 25) are know compounds and procedures for their preparation can be found in the following: for 8, 9, 12, 25, see: ref. 10 and for 10, see. Banwell M.G., and Onrust R. Tetrahedron Lett. 26 (1985) 4543