Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 775-778

  Lundquist IV, Joseph T ^a   Dix, Thomas A ^a  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; AMINO ACID PRECURSOR; OMEGA BROMO 2(S) AZIDO ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; UNITED STATES;

EID: 0032546098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10608-6     Document Type: Article

References (8)

1. 1. This paper was presented at the 214th ACS National Meeting & Exposition Program, Medicinal Chemistry Section, Las Vegas, Nevada, September 10, 1997.
2. 2. Nollet, A. J. H.; Huting, C. M.; Pandit, U. K. Tetrahedron 1969, 25, 5971.
3. 3. Servigne, M.; Szarvasi, E. Bull. Soc. Chim. Biol. 1954, 36, 1093.
4. 4. Evans, D. A.; Britton, T. C.; Ellman, J. C.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011.
5. 5. Kennedy, K. J.; Lundquist, J. T., IV; Simandan, T. L.; Beeson, C. C.; Dix, T. A. Bioorganic Med. Chem. Letts. 1997, 7, 1937.
6. 6. March, J. Advanced Organic Chemistry. Reactions, Mechanism and Structure; Third Edition, John Wiley & Sons, New York, 1985, pp 364-365.
7. 7. Lundquist, J. T., IV; Dix, T. A., unpublished results.
8. 1H-NMR spectra for these compounds is similar to 3a-3c, the only major difference being δ 3.00 (m, 2 H) for 2a-2c and δ 4.97-4.98 (dd, 1 H) for 3a-3c on the α-carbon, respectively.