Lewis acid mediated functionalization of β-lactams: mechanistic study and synthesis of C-3 unsymmetrically disubstituted azetidin-2-ones

Tetrahedron Letters

Volumn 47, Issue 30, 2006, Pages 5255-5259

  Bhalla, Aman ^a   Rathee, Suman ^a   Madan, Sachin ^a   Venugopalan, Paloth ^a   Bari, Shamsher S ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

Azetidin 2 ones; Lewis acid; Monosubstituted lactams; Nucleophiles; Unsymmetrically disubstituted azetidin 2 ones

Indexed keywords

AROMATIC COMPOUND; AZETIDINE DERIVATIVE; BETA LACTAM DERIVATIVE; CATION; LEWIS ACID;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33745190270     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.160     Document Type: Article

References (29)

1. For reviews on β-lactam antibiotics, see:. Durckheimer W., Blumbatch J., Lattrell R., and Scheunrmann K.H. Angew. Chem., Int. Ed. Engl. 24 (1985) 180-202
2. Chu D.T.W., Plattner J.J., and Katz L. J. Med. Chem. 39 (1996) 3853-3874
3. In: Morin R.B., and German M. (Eds). Chemistry and Biology of β-Lactam Antibiotics (1982), Academic, New York, NY
4. Coulton S., and Hunt E. In: Lukaes G. (Ed). Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products (1993), Springer, Berlin 621
5. Southgate R. Contemp. Org. Synth. 1 (1994) 417-432
6. In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Chapman and Hall, London
7. For comprehensive general reviews, see:. de Kimpe N. In: Padwa A. (Ed). Comprehensive Heterocyclic Chemistry II (1996), Elsevier, Oxford, UK 536-575
8. Koppel G.A. In: Hassner A. (Ed). Chemistry of Heterocyclic Compounds-Small Ring Heterocycles (1983), Wiley, New York 219
9. Burnett D.A., Caplen M.A., Davis Jr. H.R., Burrie R.E., and Clader J.W. J. Med. Chem. 37 (1994) 1733-1736
10. Han W.T., Trehan A.K., Wright J.J.K., Federici M.E., Seiler S.M., and Meanwell N.A. Bioorg. Med. Chem. 3 (1995) 1123-1143
11. Borthwick A.D., Weingarte G., Haley T.M., Tomaszewski T.M., Wang W., Hu Z., Bedard J., Jin H., Yuen L., and Mansour T.S. Bioorg. Med. Chem. Lett. 8 (1998) 365-370
12. Doherty J.B., Ashe B.M., Agrenbright L.W., Baker P.L., Bonney R.J., Chandler G.O., Dahlgren M.E., Dorn Jr. C.P., Finke P.E., Firestone R.A., Fletcher D., Hagemann W.K., Munford R., O'Grady L., Maycock A.L., Pisano J.M., Shah S.K., Thompson K.R., and Zimmerman M. Nature 322 (1986) 192-194
13. Cvetovich R.J., Chartran M., Hartner F.W., Roberge C., Amato J.S., and Grabowski E.J. J. Org. Chem. 61 (1996) 6575-6580
14. Zhou N.E., Guo D., Thomas G., Reddy A.V.N., Kaleta J., Purisima E., Menard R., Micetich R.G., and Singh R. Bioorg. Med. Chem. Lett. 13 (2003) 139-141
15. Setti E.L., Davis D., Chung T., and McCarter J. Bioorg. Med. Chem. Lett. 13 (2003) 2051-2053
16. Smith D.M., Kazi A., Smith L., Long T.E., Heldreth B., Turos E., and Dou Q.P. Mol. Pharmacol. 01 (2002) 1348-1358
17. For selected reviews, see:. Alcaide B., and Almenderos P. Synlett (2002) 381-393
18. Palomo C., Aizpurua J.M., Ganboa I., and Oiarbide M. Synlett (2001) 1813-1826
19. Alcaide B., and Almenderos P. Chem. Soc. Rev. 30 (2001) 226-240
20. Palomo C., Aizpurua J.M., Ganboa I., and Oiarbide M. Amino Acids 16 (1999) 321
21. Manhas M.S., Wagle D.R., Chiang J., and Bose A.K. Heterocycles 27 (1998) 1755
22. Clader J.W., Burnett D.A., Caplen M.A., Domalski M.S., Dugar S., Vaccaro W., Sher R., Browne M.E., Zhao H., Burrier R.E., Salisbury B., and Davis Jr. H.R. J. Med. Chem. 39 (1996) 3684-3693
23. Madan S., Arora R., Venugopalan P., and Bari S.S. Tetrahedron Lett. 41 (2000) 5577-5581
24. Bari S.S., Venugopalan P., and Arora R. Tetrahedron Lett. 44 (2003) 895-897
25. 12,13 were prepared by the procedures described in the cited references.
26. 2 = 0.0970 for 3387 reflections [I > 2σ(I)]; T = 293(2) K; GOF = 1.023. Crystallographic data (excluding structure factors) for the structure 3a in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 604665.
27. 2 = 0.0994 for 2924 reflections [I > 2σ(I)]; T = 293(2) K; GOF = 1.012. Crystallographic data (excluding structure factors) for the structure 4a in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 604666.
28. 3: C, 79.97; H, 5.79; N, 3.21%; Found: C, 80.04; H, 5.73; N, 3.17%.
29. 2 = 0.1023 for 2550 reflections [I > 2σ(I)]; T = 293(2) K; GOF = 1.012. Crystallographic data (excluding structure factors) for the structure 7b in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 604667.