A stereoselective synthesis of bis-β-amino acids

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 3919-3921

  Adamczyk, Maciej ^a   Reddy, Rajarathnam E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID;

AMINO ACID SYNTHESIS; ARTICLE; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032573435     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00429-7     Document Type: Article

References (22)

1. For reviews see (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapmann and Hall: New York, 1985. (b) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117. (e) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
2. For reviews see (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapmann and Hall: New York, 1985. (b) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117. (e) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
3. For reviews see (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapmann and Hall: New York, 1985. (b) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117. (e) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
4. For reviews see (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapmann and Hall: New York, 1985. (b) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117. (e) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
5. For reviews see (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapmann and Hall: New York, 1985. (b) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117. (e) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
6. (a) Hruby, V. J.; Bonner, G. G. In Methods in Molecular Biology, Vol. 35: Peptide Synthesis Protocols; Pennington, M. W.; Dunn, B. M., Eds; Humana Press: New Jersey, 1994, p. 201.
7. (b) Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054.
8. Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015.
9. Davis, F. A.; Reddy, R. T.; Reddy, R. E. J. Org. Chem. 1992, 57, 6337.
10. (b) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037.
11. (a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229.
12. (b) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
13. The bis-sulfinimine 3a was purified by silica gel column chromatography (30% ethyl acetate in hexanes) and 3b-c were purified by crystallization (twice) from ethyl acetate.
14. 13C NMR, mass spectrometry and HPLC and the yield referred to the spectroscopically homogeneous materials.
15. 3).
16. 3).
17. 3).
18. S,R)-4 isomer.
19. -1 at 254 nm.
20. S,S)-4a-c using trifluoroacetic acid in methanol gave the corresponding meso-bis-β-amino esters (5a-c) as bis-TFA salts in 75-91% yield with no optical rotation.
21. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
22. -1 at 254 nm.