메뉴 건너뛰기




Volumn 67, Issue 20, 2002, Pages 7004-7013

Efficient entry to highly functionalized β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction of 2-azetidinone-tethered nitrones. Synthetic applications

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITY;

EID: 0037019993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025924e     Document Type: Article
Times cited : (61)

References (70)
  • 15
    • 0034725874 scopus 로고    scopus 로고
    • Recent aspects of the chemistry of β-lactams-II
    • Miller, M. J., Ed.; Recent Aspects of the Chemistry of β-Lactams-II. Tetrahedron 2000, 56, 5553-5742.
    • (2000) Tetrahedron , vol.56 , pp. 5553-5742
    • Miller, M.J.1
  • 19
    • 0000629986 scopus 로고
    • Intermolecular 1,3-dipolar cycloadditions
    • Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, Chapter 9
    • (d) Padwa, A. Intermolecular 1,3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 9, pp 1069-1109.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069-1109
    • Padwa, A.1
  • 20
    • 0002108906 scopus 로고
    • Padwa, A., Ed.; Wiley: New York, Chapter 9
    • (e) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, Chapter 9, pp 83-168.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 83-168
    • Tufariello, J.J.1
  • 40
    • 2142816699 scopus 로고    scopus 로고
    • For recent reviews on the ketene-imine approach to β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, New York, 1993; Chapter 3, p 295. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503. (e) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
    • (1999) Eur. J. Org. Chem. , pp. 223
    • Palomo, C.1    Aizpurua, J.M.2    Ganboa, I.3    Oiarbide, M.4
  • 41
    • 0003828015 scopus 로고
    • Wiley, New York
    • For recent reviews on the ketene-imine approach to β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, New York, 1993; Chapter 3, p 295. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503. (e) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
    • (1995) Ketenes , pp. 518-527
    • Tidwell, T.T.1
  • 42
    • 0002674759 scopus 로고
    • Georg, G. I., Ed.; VCH: Weinheim, New York; Chapter 3
    • For recent reviews on the ketene-imine approach to β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, New York, 1993; Chapter 3, p 295. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503. (e) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
    • (1993) The Organic Chemistry of β-Lactams , pp. 295
    • Georg, G.I.1    Ravikumar, V.T.2
  • 43
    • 0026014624 scopus 로고
    • For recent reviews on the ketene-imine approach to β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, New York, 1993; Chapter 3, p 295. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503. (e) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
    • (1991) Tetrahedron , vol.47 , pp. 7503
    • Van der Steen, F.H.1    Van Koten, G.2
  • 44
    • 0002045618 scopus 로고
    • Trost, B., Fleming, I., Eds.; Pergamon: Oxford
    • For recent reviews on the ketene-imine approach to β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, New York, 1993; Chapter 3, p 295. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503. (e) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 85
    • Ghosez, L.1    Marchand-Brynaert, J.2
  • 45
    • 2142650244 scopus 로고    scopus 로고
    • note
    • +).
  • 47
    • 0036214613 scopus 로고    scopus 로고
    • For a review on the synthesis and biological properties of bicyclic-β-lactams with nonclassical structure, see: Alcaide, B.; Almendros, P. Curr. Org. Chem. 2002, 6, 245.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 245
    • Alcaide, B.1    Almendros, P.2
  • 50
    • 0034177426 scopus 로고    scopus 로고
    • This study showed by molecular orbital calculations that the energy differences between the HOMO of hetaryl nitrones and the LUMO of methyl acrylate were smaller than that of the opposite combination (LUMO of nitrone and HOMO of dipholarophile). As a consequence, isoxazolidine-5-carboxylate regioisomers were obtained preferentially. See: (a) Merino, P.; Anoro, S.; Merchán, F.; Tejero, T. Heterocycles 2000, 53, 861. (b) Tejero, T.; Dondoni, A.; Rojo, I.; Merchán, F. L.; Merino, P. Tetrahedron 1997, 53, 3301.
    • (2000) Heterocycles , vol.53 , pp. 861
    • Merino, P.1    Anoro, S.2    Merchán, F.3    Tejero, T.4
  • 51
    • 0031550854 scopus 로고    scopus 로고
    • This study showed by molecular orbital calculations that the energy differences between the HOMO of hetaryl nitrones and the LUMO of methyl acrylate were smaller than that of the opposite combination (LUMO of nitrone and HOMO of dipholarophile). As a consequence, isoxazolidine-5-carboxylate regioisomers were obtained preferentially. See: (a) Merino, P.; Anoro, S.; Merchán, F.; Tejero, T. Heterocycles 2000, 53, 861. (b) Tejero, T.; Dondoni, A.; Rojo, I.; Merchán, F. L.; Merino, P. Tetrahedron 1997, 53, 3301.
    • (1997) Tetrahedron , vol.53 , pp. 3301
    • Tejero, T.1    Dondoni, A.2    Rojo, I.3    Merchán, F.L.4    Merino, P.5
  • 53
    • 2142818120 scopus 로고    scopus 로고
    • note
    • 2 (SHELXTL version 5.1). The non-hydrogen atoms were refined anisotropically. The hydrogen atoms were refined the coordinates only. Further crystallographic details for the structure reported in this paper may be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K. on quoting the depository number CCDC 184077.
  • 54
    • 2142815247 scopus 로고    scopus 로고
    • note
    • Compounds 18a and 18b can also be obtained in one-pot from nitrones 3a and 3e, although in lower yields, by reaction of the appropriate nitrone with methyl propiolate in refluxing toluene.
  • 55
    • 0033800394 scopus 로고    scopus 로고
    • Aziridines are useful building blocks in organic synthesis. For reviews, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: Oxford, 1996; Vol. 1A, p 1. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469.
    • (2000) Synthesis , pp. 1347
    • McCoull, W.1    Davis, F.A.2
  • 56
    • 0002054640 scopus 로고    scopus 로고
    • Padwa, A., Ed.; Pergamon: Oxford
    • Aziridines are useful building blocks in organic synthesis. For reviews, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: Oxford, 1996; Vol. 1A, p 1. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 A , pp. 1
    • Pearson, W.H.1    Lian, B.W.2    Bergmeier, S.C.3
  • 57
    • 33748605775 scopus 로고
    • Aziridines are useful building blocks in organic synthesis. For reviews, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: Oxford, 1996; Vol. 1A, p 1. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 599
    • Tanner, D.1
  • 58
    • 0000567366 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Aziridines are useful building blocks in organic synthesis. For reviews, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: Oxford, 1996; Vol. 1A, p 1. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 469
    • Kemp, J.E.G.1
  • 60
    • 2142696709 scopus 로고
    • Taylor, E. C., Weissberger, A., Eds.; Wiley: New York
    • Vicinal coupling constants values of 6-7 Hz are typical for cis-2,3-disubstituted aziridines. See, for example: Batterham, T. J. In NMR Spectra of Simple Heterocycles; Taylor, E. C., Weissberger, A., Eds.; Wiley: New York, 1973; p 139.
    • (1973) MR Spectra of Simple Heterocycles , pp. 139
    • Batterham, T.J.1
  • 61
    • 0028108201 scopus 로고
    • For use as psychotropic agents, see: (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36. For use as antihypertensive agents, see: (c) Bergmann, R.; Gericke, R, J. Med. Chem. 1990, 33, 492. For use as inhibitors of proteolytic catalysis, see: (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1. For use as antimuscarinic agents, see: (e) Nilsson, B. M.; Ringdhal, B.; Hacksell, U. A. J. Med. Chem. 1990, 33, 580.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7277
    • Moody, C.M.1    Young, D.W.2
  • 62
    • 0027535582 scopus 로고
    • For use as psychotropic agents, see: (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36. For use as antihypertensive agents, see: (c) Bergmann, R.; Gericke, R, J. Med. Chem. 1990, 33, 492. For use as inhibitors of proteolytic catalysis, see: (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1. For use as antimuscarinic agents, see: (e) Nilsson, B. M.; Ringdhal, B.; Hacksell, U. A. J. Med. Chem. 1990, 33, 580.
    • (1993) J. Org. Chem. , vol.58 , pp. 36
    • Meyers, A.I.1    Snyder, L.2
  • 63
    • 0025015260 scopus 로고
    • For use as psychotropic agents, see: (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36. For use as antihypertensive agents, see: (c) Bergmann, R.; Gericke, R, J. Med. Chem. 1990, 33, 492. For use as inhibitors of proteolytic catalysis, see: (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1. For use as antimuscarinic agents, see: (e) Nilsson, B. M.; Ringdhal, B.; Hacksell, U. A. J. Med. Chem. 1990, 33, 580.
    • (1990) J. Med. Chem. , vol.33 , pp. 492
    • Bergmann, R.1    Gericke, R.2
  • 64
    • 0033022744 scopus 로고    scopus 로고
    • For use as psychotropic agents, see: (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36. For use as antihypertensive agents, see: (c) Bergmann, R.; Gericke, R, J. Med. Chem. 1990, 33, 492. For use as inhibitors of proteolytic catalysis, see: (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1. For use as antimuscarinic agents, see: (e) Nilsson, B. M.; Ringdhal, B.; Hacksell, U. A. J. Med. Chem. 1990, 33, 580.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1
    • Corey, E.J.1    Li, W.-D.Z.2
  • 65
    • 0025159307 scopus 로고
    • For use as psychotropic agents, see: (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36. For use as antihypertensive agents, see: (c) Bergmann, R.; Gericke, R, J. Med. Chem. 1990, 33, 492. For use as inhibitors of proteolytic catalysis, see: (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1. For use as antimuscarinic agents, see: (e) Nilsson, B. M.; Ringdhal, B.; Hacksell, U. A. J. Med. Chem. 1990, 33, 580.
    • (1990) J. Med. Chem. , vol.33 , pp. 580
    • Nilsson, B.M.1    Ringdhal, B.2    Hacksell, U.A.3
  • 70
    • 2142815246 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.