Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from L-aspartic acid

Tetrahedron

Volumn 52, Issue 39, 1996, Pages 12839-12852

  Shibata, Norio ^a   Baldwin, Jack E ^a   Jacobs, Adam ^a   Wood, Mark E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 MERCAPTOASPARTIC ACID; ASPARTIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030599240     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00765-X     Document Type: Article

References (16)

1. 1. Shibata, N.; Baldwin, J. E.; Jacobs, A.; Wood, M. E. Synlett 1996, 519-520.
2. 2. Hauptmann, H.; Berl, H. J. Am. Chem. Soc. 1955, 77, 704-707.
3. 3. Baldwin, J. E.; Moloney, M. G.; North, M. J. Chem. Soc., Perkin Trans. 1 1989, 833-834; Tetrahedron 1989, 45, 6309-6318; Tetrahedron 1989, 45, 6319-6330.
4. 3. Baldwin, J. E.; Moloney, M. G.; North, M. J. Chem. Soc., Perkin Trans. 1 1989, 833-834; Tetrahedron 1989, 45, 6309-6318; Tetrahedron 1989, 45, 6319-6330.
5. 3. Baldwin, J. E.; Moloney, M. G.; North, M. J. Chem. Soc., Perkin Trans. 1 1989, 833-834; Tetrahedron 1989, 45, 6309-6318; Tetrahedron 1989, 45, 6319-6330.
6. 4. Scholz, D. Synthesis 1983, 944-945.
7. 5. Stevens, C. M.; Watanabe, R. J. Am. Chem. Soc. 1950, 72, 725-727.
8. 6. Kileger, E.; Gibian, H. Liebigs Ann. Chem. 1962, 655, 195-210.
9. 7. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522-524.
10. 8. The absolute stereochemistry of the newly generated stereogenic centre was not determined in either case.
11. 9. Sakakibara, S.; Nobuhara, Y.; Shimonishi, Y.; Kiyoi, R. Bull. Chem. Soc. Jpn. 1965, 38, 120-123.
12. 10. X-ray crystallographic data has been deposited at the Cambridge Crystallographic Data Centre.
13. 11. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 2nd ed., Wiley: New York, 1991.
14. 12. 24 was prepared by methodology frequently used in our group. For example see: Marquess, D. D. Phil. Thesis, University of Oxford, 1992.
15. 13. Nishimura, O.; Kitada, C.; Fujino, M. Chem. Pharm. Bull. 1978, 26, 1576-1585.
16. 14. Baldwin, J. E.; Schofield, C. J. In The Chemistry of β-Lactams; Page, M. I., Ed., Blackie: London, 1992; Chapter 1.