PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams: Effect of chain length and stereochemistry on the enantioselectivity

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6529-6538

  Basak, Amit ^a,b   Bhattacharya, Gautam ^a   Bdour, Hussam M M ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032482302     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00313-5     Document Type: Article

References (15)

1. 1. Boland, W.: Fropil, C.: Loreng, M. Synthesis 1991, 1049.
2. 2. Gutman, A. L.: Bravdo, T. J. Org. Chem. 1989, 54, 4263.
3. 3. Cambou, B.; Klibanov, A. M. J. Am. Chem. Soc. 1984, 106, 2687.
4. 4. Ehrler, J.; Seebach, D. Liebigs Ann. Chem. 1990, 379.
5. 5. Hultin, P. G.: Jones, J. B. Tetrahedron Lett. 1992, 33, 1399.
6. 6 Brieva, R.: Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068; Ojima, I.; Habus, I; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigand, I. Tetrahedron 1992, 48, 6985.
7. 6 Brieva, R.: Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068; Ojima, I.; Habus, I; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigand, I. Tetrahedron 1992, 48, 6985.
8. 7. Palemo, C.; Arrieta., A.; Cossio, F. P.; Aizpurua, J. M.; Mìelgo, A.; Aurrekotxea, N. Tetrahedron Lett. 1990, 31, 6429.
9. 8. A preliminary communication has been published: Basak, A.; Mahato, T.; Bhattacharya, G.; Mukherjee, B Tetrahedron Lett. 1997, 38, 643.
10. 9. Kinugasa, M.; Hashimoto, S. J. Chem. Soc. Chem. Commun. 1972, 466; Ding, L. K.; Irwin, W. J. J. Chem. Soc. Perkin Trans. 1 1976.
11. 9. Kinugasa, M.; Hashimoto, S. J. Chem. Soc. Chem. Commun. 1972, 466; Ding, L. K.; Irwin, W. J. J. Chem. Soc. Perkin Trans. 1 1976.
12. 10. Wong, C. H.; Whiteside, G. M. Ed. Enzymes in Organic Chemistry, Pergamon Press, Oxford, 1994.
13. 11. Frase, R. R.; Petit, M. A.; Soundrea, J. K. J. Chem. Soc. Chem. Commun. 1971, 1450.
14. 12. Galle, D.; Tolkssdorf, M.; Braun, M. Tetrahedron Lett. 1995, 36, 4217.
15. 13. Miura, M.; Enna, M.; Okura, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.