Efficient synthesis of β-amino bromides

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3011-3014

  Nagle, Advait S ^a   Salvatore, Ralph N ^a   Chong, Byong Don ^a   Woon Jung, Kyung ^a,b  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

Author keywords

amino bromide; Aziridinium salt; Bromination; DMF; Thionyl bromide

Indexed keywords

AZIRIDINE DERIVATIVE; BROMINE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION KINETICS; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034701535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00330-0     Document Type: Article

References (15)

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2. For comprehensive reviews on aminoalcohols and related compounds, see: (a) see Ref. 1.
3. For comprehensive reviews on aminoalcohols and related compounds, see: (b) Reetz, M. T. Chem. Rev. 1999, 99, 1121.
4. For comprehensive reviews on aminoalcohols and related compounds, see: (c) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
5. For our N-alkylation, see: Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893.
6. Cortese, F. Organic Syntheses; John Wiley: New York, 1943; Vol. II, pp. 91-93.
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8. 4, filtered, and concentrated in vacuo to afford the desired N,N-dibenzylamino bromide as a yellow oil.
9. The stereochemistry of the bromides was elucidated by either proton NMR analysis or comparison with authentic samples. Enantioselectivities and diastereoselectivities were confirmed through Mosher's esters, which were prepared with (S)-MTPA acid using our cesium base promoted O-alkylation techniques. For our O-alkylations, see: (a) Parrish, J. P.; Sundaresan, B.; Jung, K. W. Synth. Commun. 1999, 29, 4423.
10. The stereochemistry of the bromides was elucidated by either proton NMR analysis or comparison with authentic samples. Enantioselectivities and diastereoselectivities were confirmed through Mosher's esters, which were prepared with (S)-MTPA acid using our cesium base promoted O-alkylation techniques. For our O-alkylations, see: (b) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843.
11. The stereochemistry of the bromides was elucidated by either proton NMR analysis or comparison with authentic samples. Enantioselectivities and diastereoselectivities were confirmed through Mosher's esters, which were prepared with (S)-MTPA acid using our cesium base promoted O-alkylation techniques. For our O-alkylations, see: (c) Chu, F.; Dueno, E. E.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1847.
12. The stereochemistry of the bromides was elucidated by either proton NMR analysis or comparison with authentic samples. Enantioselectivities and diastereoselectivities were confirmed through Mosher's esters, which were prepared with (S)-MTPA acid using our cesium base promoted O-alkylation techniques. For our O-alkylations, see: (d) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578.
13. cis-2-Aminocyclohexanol was prepared from the trans isomer. (a) Leffler, M. T.; Adams, R. J. Am. Chem Soc. 1937, 59, 2252.
14. cis-2-Aminocyclohexanol was prepared from the trans isomer. (b) McCasland, G. E.; Clark Jr., R. K.; Carter, H. E. J. Am. Chem. Soc. 1949, 71, 637.
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