V. V. Govande, A. R. A. S. Deshmukh / Tetrahedron Letters 45 (2004) 6563–6566
6565
H
H
N
H
H
N
1O
1O
R
R
CCl3
R
CCl3
R
H
O
CH2Cl2, DIEA
0 ˚C to rt, 15 h
R
R1O
+
+
N
Cl3C
Cl
O
O
3
6
7
8
Scheme 2.
Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1996, 6,
1271–1274; (c) Wu, G. G. Org. Process Res. Dev. 2000, 4,
298–300.
various acid chlorides provided selectively cis-4-trichloro-
methyl azetidin-2-ones in moderate to good yields.
9. (a) Doherty, J. B.; Ashe, B. M.; Agrenbright, L. W.;
Barker, P. L.; Bonney, R. J.; Chandler, G. O.; Dahlgren,
M. E.; Dorn, C. P., Jr.; Finke, P. E.; Firestone, R. A.;
Fletcher, D.; Hagemann, W. K.; Munford, R.; OÕGrady,
L.; Maycock, A. L.; Pisano, J. M.; Shah, S. K.; Thomson,
K. R.; Zimmerman, M. Nature 1986, 322, 192–194; (b)
Cvetovich, R. J.; Chartran, M.; Hartner, F. W.; Roberge,
C.; Amato, J. S.; Grabowski, E. J. J. Org. Chem. 1996, 61,
6575–6580.
Acknowledgements
The authors thank the Department of Science and Tech-
nology, New Delhi for financial support and V.V.G.
thanks CSIR, New Delhi for a research fellowship.
References and notes
10. (a) Zhou, N. E.; Guo, D.; Thomas, G.; Reddy, A. V. N.;
Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R. G.;
Singh, R. Bioorg. Med. Chem. Lett. 2003, 13, 139–141; (b)
Setti, E. L.; Davis, D.; Chung, T.; McCarter, J. Bioorg.
Med. Chem. Lett. 2003, 13, 2051–2053.
11. Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51–123.
12. (a) Palomo, C.; Aizpurua, J.; Mielgo, A.; Linden, A. J.
Org. Chem. 1996, 61, 9186–9195; (b) Palomo, C.; Aizpu-
rua, J. M.; Ganboa, I.; Oirabide, M. Eur. J. Org. Chem.
1999, 8, 3223–3235; (c) Alcaide, B.; Almendros, P. Chem.
Soc. Rev. 2001, 30, 226–240.
1. For reviews on b-lactam antibiotics, see: (a) Durkheimer,
¨
W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H.
Angew. Chem., Int. Ed. Engl. 1985, 24, 180–202; (b)
Chemistry and Biology of b-Lactam Antibiotics; Morin, R.
B., Gorman, M., Eds.; Academic: New York, 1982; Vols.
1–3; (c) Coulton, S.; Hunt, E. In Recent Progress in the
Chemical Synthesis of Antibiotics and Related Microbial
Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p
621; (d) Southgate, R. Contemp. Org. Synth. 1994, 1,
417–432.
13. (a) Govande, V. V.; Arun, M.; Deshmukh, A. R. A. S.;
Bhawal, B. M. Synth. Commun. 2000, 30, 4177–4182; (b)
Joshi, S. N.; Deshmukh, A. R. A. S.; Bhawal, B. M.
Tetrahedron: Asymmetry 2000, 11, 1477–1485; (c) Krishna-
swamy, D.; Bhawal, B. M.; Deshmukh, A. R. A. S.
Tetrahedron Lett. 2000, 41, 417–419; (d) Thiagarajan, K.;
Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M.
Tetrahedron 2000, 56, 7811–7816; (e) Karupaiyan, K.;
Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M.
Tetrahedron 2000, 56, 8555–8560; (f) Bhawal, B. M.; Joshi,
S. N.; Krishnaswamy, D.; Deshmukh, A. R. A. S. J.
Indian Inst. Sci. 2001, 81, 265–276; (g) Joshi, S. N.;
Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M.
Tetrahedron: Asymmetry 2001, 12, 3073–3076; (h) Arun,
M.; Govande, V. V.; Deshmukh, A. R. A. S.; Bhawal, B.
M. Indian J. Chem. 2002, 41B, 856–857; (i) Krishnaswamy,
D.; Govande, V. V.; Gumaste, V. K.; Bhawal, B. M.;
Deshmukh, A. R. A. S. Tetrahedron 2002, 58, 2215–2225;
(j) Patil, R. T.; Parveen, G.; Gumaste, V. K.; Bhawal, B.
M.; Deshmukh, A. R. A. S. Synlett 2002, 1455–1458; (k)
Joshi, S. N.; Phalgune, U. D.; Bhawal, B. M.; Deshmukh,
A. R. A. S. Tetrahedron Lett. 2003, 44, 1827–1830; (l)
Arun, M.; Joshi, S. N.; Puranik, V. G.; Bhawal, B. M.;
Deshmukh, A. R. A. S. Tetrahedron 2003, 59, 2309–2316;
(m) Shinkre, B. A.; Puranik, V. G.; Bhawal, B. M.;
Deshmukh, A. R. A. S. Tetrahedron: Asymmetry 2003, 14,
453–459; (n) Jayanthi, A.; Gumaste, V. K.; Deshmukh, A.
R. A. S. Synlett 2004, 979–982.
2. The Chemistry of b-Lactams; Page, M. I., Ed.; Chapman
and Hall: London, 1992.
3. For comprehensive general reviews, see: (a) Koppel, G. A.
In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New
York, 1983; Vol. 42; p 219; (b) Backes, J. In Houben-Weyl,
Methoden der Organischem Chemie; Muller, E., Bayer, O.,
Eds.; Thieme: Stuttgart, 1991; Band E16B, p 31; (c) de
Kimpe, N. In Comprehensive Heterocyclic Chemistry II;
Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Padwa,
A., Eds.; Pergamon: Oxford, 1996; Vol. 1B, p 507.
4. (a) Ojima, I. In The Chemistry of b-Lactams; Georg, G. I.,
Ed.; VCH: New York, 1993; p 197; (b) Palomo, C.;
Aizpurua, J.; Ganboa, I. In Enantioselective Synthesis of
Beta-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New
York, 1997; p 279, and references cited therein; For a
review on this subject see: (c) Ojima, I.; Delaloge, F.
Chem. Soc. Rev. 1997, 26, 377–386; (d) Alcaide, B.;
Almendros, P. Chem. Soc. Rev. 2001, 30, 226–240; (e)
Alcaide, B.; Almendros, P. Synlett 2002, 381–393.
5. Adlington, R. M.; Baldwin, J. E.; Chen, B.; Cooper, S. L.;
McCoull, W.; Pritchard, G. J.; Howe, T. J.; Becker, G. W.;
Hermann, R. B.; McNulty, A. M.; Neubauer, B. L.
Bioorg. Med. Chem. Lett. 1997, 7, 1689–1694.
6. Han, W. T.; Trehan, A. K.; Kim Wright, J. J.; Federeci,
M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem.
1995, 3, 1123–1143.
7. Borthwick, A. D.; Weingarten, G.; Haley, T. M.; Tom-
aszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jih, H.; Yuen,
L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8,
365–370.
8. (a) Burnett, D. A.; Caplen, M. A.; Davis, H. R., Jr.;
Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37,
1733–1736; (b) Dugar, S.; Yumibe, N.; Clader, J. W.;
Vizziano, M.; Huie, K.; van Heek, M.; Compton, D. S.;
14. (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M.
Tetrahedron 1996, 52, 8989–9004; (b) Jayaraman, M.;
Puranik, V. G.; Bhawal, B. M. Tetrahedron 1996, 52,
9005–9016; (c) Srirajan, V.; Deshmukh, A. R. A. S.;
Puranik, V. G.; Bhawal, B. M. Tetrahedron: Asymmetry
1996, 7, 2733–2738; (d) Krishnaswamy, D.; Govande, V.
V.; Deshmukh, A. R. A. S. Synthesis 2003, 12, 1903–1908.