Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5077-5080

  Banik, Bimal K ^a   Manhas, Maghar S ^a   Bose, Ajay K ^a  

^a Stevens Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; ENANTIOMER; GLYCOSYLATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030834192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01130-1     Document Type: Article

References (21)

1. Studies on Lactams Part 103; for Part 102, see Jayaraman, M.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett, 1997, 38, 709.
2. For some recent publications on the synthesis of the taxol side chain, see: (a) Hattori, K; Yamamoto, H. Tetrahedron Lett. 1994, 50, 2785.
3. (b) Brieva, R.; Crich, J. Z.; Sih, C. J. Org. Chem. 1993, 55, 1068.
4. (c) Kanazawa, A. M.; Correa, A.; Dennis, J. N.; Luche, M. J.; Green, A. E. J. Org. Chem. 1993, 58, 255 and references cited therein,
5. (d) Also see, Ojima, I. Acc. Chem. Res. 1995, 28, 383 and references cited therein.
6. (a) Bose, A. K.; Mathur, C.; Wagle, D. R.; Naqvi, R.; Manhas, M. S. Heterocycles, 1995, 491.
7. (b) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307 and references cited therein.
8. (c) also see, Ojima, I. In The Organic Chemistry of β-Lactams; Georg, G. I. Ed., VCH Publishers: New York, 1992; pp. 198-252.
9. Banik B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714.
10. Bose, A. K.; Banik, B. K.; Manhas, M. S. Tetrahedron Lett. 1995, 36, 213; also see: Endo, M.; Droghini, R. BioMed. Chem. Lett. 1993, 3, 2483.
11. Bose, A. K.; Banik, B. K.; Manhas, M. S. Tetrahedron Lett. 1995, 36, 213; also see: Endo, M.; Droghini, R. BioMed. Chem. Lett. 1993, 3, 2483.
12. For our recent work on Microwave Induced Organic Reaction Enhancement Chemistry, See: Bose, A. K.; Manhas, M. S.; Banik, B. K.; Robb, E. W. Res. Chem. Interned. 1994, 20, 1; also see: Bose, A. K.; Jayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 39, 6989; Banik, B. K.; Manhas, M. S.; Robb, E. W.; Bose, A. K. Heterocycles, 1997, 44, 405 and references cited therein.
13. For our recent work on Microwave Induced Organic Reaction Enhancement Chemistry, See: Bose, A. K.; Manhas, M. S.; Banik, B. K.; Robb, E. W. Res. Chem. Interned. 1994, 20, 1; also see: Bose, A. K.; Jayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 39, 6989; Banik, B. K.; Manhas, M. S.; Robb, E. W.; Bose, A. K. Heterocycles, 1997, 44, 405 and references cited therein.
14. For our recent work on Microwave Induced Organic Reaction Enhancement Chemistry, See: Bose, A. K.; Manhas, M. S.; Banik, B. K.; Robb, E. W. Res. Chem. Interned. 1994, 20, 1; also see: Bose, A. K.; Jayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 39, 6989; Banik, B. K.; Manhas, M. S.; Robb, E. W.; Bose, A. K. Heterocycles, 1997, 44, 405 and references cited therein.
15. For iodine catalyzed glycosylation reaction via Ferner rearrangement, see: Koreeda, M.; Houston, T. A.; Shull, B. K.; Klemke, E.; Tuinman, R. J. Synlett, 1995, 90.
16. Ferner, R. J. Adv. Carbohydr. Chem. Biochem. 1969, 199 and references cited therein.
17. The reduction of the olefinic group in 10 was conducted by catalytic transfer hydrogenation under microwave irradiation, see: Bose, A. K.; Banik, B. K.; Barakat, K. J.; Manhas, M. S. Synlett, 1993, 575.
18. 1H NMR spectrum of the hydrogenated product 12 obtained from 10 indicated the α-glycosidic linkage. See: Lemieux, R. U.; Stevens, J. D. Can. J. Chem. 1965, 43, 2059.
19. 1H NMR of 14 and 16 in the presence of a chiral shift reagent confirmed the absolute configuration of these β-lactams and their mirror image relationship.
20. All new compounds described here gave satisfactory spectral and elemental analyses.
21. 4N: C, 71.91; H, 6.85; N, 3.81. Found: C, 71.80; H, 6.73; N, 3.64.