Facile stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones

Tetrahedron Letters

Volumn 45, Issue 35, 2004, Pages 6563-6566

  Govande, V V ^a   Deshmukh, A R A S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Azetidin 2 ones; Imines; Ketenes; Staudinger reaction

Indexed keywords

AZETIDINE DERIVATIVE; CHLORAL; IMINE; KETENE DERIVATIVE;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 4143053365     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.047     Document Type: Article

References (64)

1. For reviews on β-lactam antibiotics, see: W. Dürkheimer, J. Blumbach, R. Lattrell, and K.H. Scheunemann Angew. Chem., Int. Ed. Engl. 24 1985 180 202
2. R.B. Morin M. Gorman Chemistry and Biology of β-Lactam Antibiotics Vols. 1-3 1982 Academic New York
3. S. Coulton, and E. Hunt G. Lukacs Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2 1993 Springer Berlin 621
4. R. Southgate Contemp. Org. Synth. 1 1994 417 432
5. M.I. Page The Chemistry of β-Lactams 1992 Chapman and Hall London
6. For comprehensive general reviews, see: G.A. Koppel A. Hasner Small Ring Heterocycles Vol. 42 1983 Wiley New York 219
7. J. Backes E. Muller O. Bayer Houben-Weyl, Methoden der Organischem Chemie Band E16B 1991 Thieme Stuttgart 31
8. N. de Kimpe A.R. Katritzky C.W. Rees E.F.V. Scriven A. Padwa Comprehensive Heterocyclic Chemistry II Vol. 1B 1996 Pergamon Oxford 507
9. I. Ojima G.I. Georg The Chemistry of β-Lactams 1993 VCH New York p 197
10. C. Palomo, J. Aizpurua, and I. Ganboa E. Juaristi Enantioselective Synthesis of Beta-Amino Acids 1997 Wiley-VCH New York p 279, and references cited therein
11. For a review on this subject see: I. Ojima, and F. Delaloge Chem. Soc. Rev. 26 1997 377 386
12. B. Alcaide, and P. Almendros Chem. Soc. Rev. 30 2001 226 240
13. B. Alcaide, and P. Almendros Synlett 2002 381 393
14. R.M. Adlington, J.E. Baldwin, B. Chen, S.L. Cooper, W. McCoull, G.J. Pritchard, T.J. Howe, G.W. Becker, R.B. Hermann, A.M. McNulty, and B.L. Neubauer Bioorg. Med. Chem. Lett. 7 1997 1689 1694
15. W.T. Han, A.K. Trehan, J.J. Kim Wright, M.E. Federeci, S.M. Seiler, and N.A. Meanwell Bioorg. Med. Chem. 3 1995 1123 1143
16. A.D. Borthwick, G. Weingarten, T.M. Haley, M. Tomaszewski, W. Wang, Z. Hu, J. Bedard, H. Jih, L. Yuen, and T.S. Mansour Bioorg. Med. Chem. Lett. 8 1998 365 370
17. D.A. Burnett, M.A. Caplen, H.R. Davis Jr., R.E. Burrier, and J.W. Clader J. Med. Chem. 37 1994 1733 1736
18. S. Dugar, N. Yumibe, J.W. Clader, M. Vizziano, K. Huie, M. van Heek, D.S. Compton, and H.R. Davis Jr. Bioorg. Med. Chem. Lett. 6 1996 1271 1274
19. G.G. Wu Org. Process Res. Dev. 4 2000 298 300
20. J.B. Doherty, B.M. Ashe, L.W. Agrenbright, P.L. Barker, R.J. Bonney, G.O. Chandler, M.E. Dahlgren, C.P. Dorn Jr., P.E. Finke, R.A. Firestone, D. Fletcher, W.K. Hagemann, R. Munford, L. O'Grady, A.L. Maycock, J.M. Pisano, S.K. Shah, K.R. Thomson, and M. Zimmerman Nature 322 1986 192 194
21. R.J. Cvetovich, M. Chartran, F.W. Hartner, C. Roberge, J.S. Amato, and E.J. Grabowski J. Org. Chem. 61 1996 6575 6580
22. N.E. Zhou, D. Guo, G. Thomas, A.V.N. Reddy, J. Kaleta, E. Purisima, R. Menard, R.G. Micetich, and R. Singh Bioorg. Med. Chem. Lett. 13 2003 139 141
23. E.L. Setti, D. Davis, T. Chung, and J. McCarter Bioorg. Med. Chem. Lett. 13 2003 2051 2053
24. H. Staudinger Liebigs Ann. Chem. 356 1907 51 123
25. C. Palomo, J. Aizpurua, A. Mielgo, and A. Linden J. Org. Chem. 61 1996 9186 9195
26. C. Palomo, J.M. Aizpurua, I. Ganboa, and M. Oirabide Eur. J. Org. Chem. 8 1999 3223 3235
27. B. Alcaide, and P. Almendros Chem. Soc. Rev. 30 2001 226 240
28. V.V. Govande, M. Arun, A.R.A.S. Deshmukh, and B.M. Bhawal Synth. Commun. 30 2000 4177 4182
29. S.N. Joshi, A.R.A.S. Deshmukh, and B.M. Bhawal Tetrahedron: Asymmetry 11 2000 1477 1485
30. D. Krishnaswamy, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron Lett. 41 2000 417 419
31. K. Thiagarajan, V.G. Puranik, A.R.A.S. Deshmukh, and B.M. Bhawal Tetrahedron 56 2000 7811 7816
32. K. Karupaiyan, V.G. Puranik, A.R.A.S. Deshmukh, and B.M. Bhawal Tetrahedron 56 2000 8555 8560
33. B.M. Bhawal, S.N. Joshi, D. Krishnaswamy, and A.R.A.S. Deshmukh J. Indian Inst. Sci. 81 2001 265 276
34. S.N. Joshi, V.G. Puranik, A.R.A.S. Deshmukh, and B.M. Bhawal Tetrahedron: Asymmetry 12 2001 3073 3076
35. M. Arun, V.V. Govande, A.R.A.S. Deshmukh, and B.M. Bhawal Indian J. Chem. 41B 2002 856 857
36. D. Krishnaswamy, V.V. Govande, V.K. Gumaste, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron 58 2002 2215 2225
37. R.T. Patil, G. Parveen, V.K. Gumaste, B.M. Bhawal, and A.R.A.S. Deshmukh Synlett 2002 1455 1458
38. S.N. Joshi, U.D. Phalgune, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron Lett. 44 2003 1827 1830
39. M. Arun, S.N. Joshi, V.G. Puranik, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron 59 2003 2309 2316
40. B.A. Shinkre, V.G. Puranik, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron: Asymmetry 14 2003 453 459
41. A. Jayanthi, V.K. Gumaste, and A.R.A.S. Deshmukh Synlett 2004 979 982
42. M. Jayaraman, A.R.A.S. Deshmukh, and B.M. Bhawal Tetrahedron 52 1996 8989 9004
43. M. Jayaraman, V.G. Puranik, and B.M. Bhawal Tetrahedron 52 1996 9005 9016
44. V. Srirajan, A.R.A.S. Deshmukh, V.G. Puranik, and B.M. Bhawal Tetrahedron: Asymmetry 7 1996 2733 2738
45. D. Krishnaswamy, V.V. Govande, and A.R.A.S. Deshmukh Synthesis 12 2003 1903 1908
46. R.L. Tennyson, G.S. Cortez, H.J. Galicia, C.R. Kreiman, C.M. Thompson, and D. Romo Org. Lett. 4 2002 533 536
47. M.H. Elnagdi, E.M. Kandeel, E.M. Zayed, and Z.E. Kandil J. Prakt. Chem. 320 1978 533 538
48. N.S. Ibrahim, E.A.A. Hafez, and R.M. Mohareb Heterocycles 24 1986 2085 2088
49. M.R.H. Elmoghayar, and A.H.H. Elghandour Monatsh. Chem. 117 1986 201 204
50. J. March Advanced Organic Chemistry 4th ed. 1992 John Wiley & Sons New York p 632
51. A.R.A.S. Deshmukh, D.G. Panse, and B.M. Bhawal Synth. Commun. 29 1999 1801 1809
52. M. Romero-Ortega, H. Reyes, A. Covarruvias-Zuniga, R. Cruz, and J.G. Avila-Zarraga Synthesis 18 2003 2765 2767
53. R. Batti, D.K. Barma, M. Krishna, C. Mioskowski, and J.R. Falck Tetrahedron Lett. 43 2002 959 961
54. R. Batti, D.K. Barma, C. Mioskowski, and J.R. Falck Tetrahedron Lett. 43 2002 2183 2185
55. J.R. Falck, A. Bandyopadhyay, D.K. Barma, D.S. Shin, A. Kundu, and R.V. Krishna Kishore Tetrahedron Lett. 45 2004 3039 3042
56. H.R. Pfaendler, J. Gosteli, R.B. Woodward, and G. Rihs J. Am. Chem. Soc. 103 1981 4526 4531
57. D.B. Boyd R.B. Morin M. Gorman Chemistry and Biology of β-Lactam Antibiotics Vol. 1 1982 Academic New York 437
58. P.F. Bevilacqua, D.D. Keith, and J.L. Roberts J. Org. Chem. 49 1984 1430 1434
59. O.P. Novikova, L.I. Livantsova, and G.S. Zaitseva Zn. Obshch. Khim. 59 1989 2630 2631
60. G. Giesemann, and I. Ugi Synthesis 10 1983 788 789
61. M. Lasperas New J. Chem. 13 1989 193 203
62. J. Bartus, W.J. Simonsick Jr., K. Hatada, and O. Vogl Polym. Prep. 33 1992 114 115
63. J. Bartus, K. Hatada, and O. Vogl Heterocycles 35 1993 181 191
64. 3 requires C, 55.08; H, 3.80; N, 3.77; Cl, 28.69. Found: C, 55.22; H, 3.76; N, 3.80; Cl, 28.60