메뉴 건너뛰기




Volumn 63, Issue 20, 1998, Pages 6786-6796

Alkyne-Co2(CO)6 complexes in the synthesis of fused tricyclic β- lactam and azetidine systems

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALKYNE; ANISIC ACID; AZETIDINE DERIVATIVE; GLYCERALDEHYDE; GLYOXAL DERIVATIVE; IMINE; PHENOXYACETIC ACID; TRIBACTAM; TRIMETHYLAMINE OXIDE;

EID: 0032476127     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980114h     Document Type: Article
Times cited : (64)

References (95)
  • 3
    • 0003089148 scopus 로고    scopus 로고
    • For excellent articles on the bacterian resistance to the common use antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333.
    • (1997) Chem. Br. , vol.33 , pp. 34
    • Hook, V.1
  • 4
    • 0030660723 scopus 로고    scopus 로고
    • For excellent articles on the bacterian resistance to the common use antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333.
    • (1997) Chem. Commun. , pp. 2333
    • Niccolai, D.1    Tarsi, L.2    Thomas, R.J.3
  • 5
    • 0001067555 scopus 로고    scopus 로고
    • Recent examples: (a) Wu, G.; Tormos, W. J. Org. Chem. 1997, 62, 6412. (b) 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.; Davis, H. R. J. Med. Chem. 1996, 39, 3684 and references therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 6412
    • Wu, G.1    Tormos, W.2
  • 10
    • 0030738040 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5913
    • Sakya, S.M.1    Strohmeyer, T.W.2    Lang, S.A.3    Lin, Y.-I.4
  • 11
    • 0030864548 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1997) Tetrahedron , vol.53 , pp. 13129
    • Annibalc, A.D.1    Pesce, A.2    Resta, S.3    Irogolo, C.T.4
  • 12
    • 0029822636 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1996) J. Org. Chem. , vol.61 , pp. 7125
    • Alcaide, B.1    Polanco, C.2    Sáez, E.3    Sierra, M.A.4
  • 13
    • 0030221457 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2203
    • Alcaide, B.1    Rodríguez-Vicente, A.2    Sierra, M.A.3
  • 14
    • 0029988586 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1363
    • Banik, B.K.1    Gottumukkala, V.2    Manhas, M.S.3    Bose, A.K.4
  • 15
    • 0013490053 scopus 로고    scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1996) J. Org. Chem. , vol.67 , pp. 1014
    • Chuansheng, N.1    Pettersson, T.2    Miller, M.J.3
  • 16
    • 0028792629 scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1995) J. Org. Chem. , vol.60 , pp. 6176
    • Crocker, P.J.1    Miller, M.J.2
  • 17
    • 0028802998 scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1995) Tetrahedron Lett. , vol.47 , pp. 8693
    • Gilchrist, T.L.1    Graham, K.2
  • 18
    • 0028120411 scopus 로고
    • Recent examples: (a) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I Tetrahedron Lett. 1997, 38, 5913. (b) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (c) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (d) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 67, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (i) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
    • (1994) BioMed. Chem. Lett. , vol.19 , pp. 2285
    • Hanessian, S.1    Reddy, B.G.2
  • 19
    • 0004015248 scopus 로고
    • Georg, G. I., Ed.; VCH Publishers: New York
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1993) The Organic Chemistry of β-Lactams
    • Kant, J.1    Walker, D.G.2
  • 20
    • 0031026885 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 15
    • Camerini, R.1    Donati, D.2    Marchioro, C.3    Mazzoni, A.4    Pachera, R.5    Panunzio, M.6
  • 21
    • 0030958694 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3587
    • Di Fabio, R.1    Rossi, T.2    Thomas, R.J.3    Thomas, R.J.4
  • 22
    • 33748659244 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 463
    • Marchioro, C.1    Pentassuglia, G.2    Perboni, A.3    Donati, D.4
  • 23
    • 0030932639 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) J. Org. Chem. , vol.62 , pp. 1653
    • Rossi, T.1    Marchiro, C.2    Paio, A.3    Thomas, R.J.4    Zarantonello, P.5
  • 24
    • 0030852692 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) BioMed. Chem. Lett. , vol.7 , pp. 1857
    • Hanessian, S.1    Griffin, A.M.2    Rozema, M.J.3
  • 25
    • 0030958478 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1997) Tetrahedron Lett. , vol.20 , pp. 3569
    • Guiron, C.1    Rossi, T.2    Thomas, R.J.3
  • 26
    • 0029961308 scopus 로고    scopus 로고
    • For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9884
    • Hanessian, S.1    Rozema, M.J.2
  • 38
    • 0001136410 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K.
    • For reviews on the P-K reaction, see: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703. (b) Schore, N. E. Org. React. 1991, 40, 1. (c) Pauson, P. L. Tetrahedron 1985, 41, 5855.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703
    • Schore, N.E.1
  • 39
    • 0002307453 scopus 로고
    • For reviews on the P-K reaction, see: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703. (b) Schore, N. E. Org. React. 1991, 40, 1. (c) Pauson, P. L. Tetrahedron 1985, 41, 5855.
    • (1991) Org. React. , vol.40 , pp. 1
    • Schore, N.E.1
  • 40
    • 0000134751 scopus 로고
    • For reviews on the P-K reaction, see: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703. (b) Schore, N. E. Org. React. 1991, 40, 1. (c) Pauson, P. L. Tetrahedron 1985, 41, 5855.
    • (1985) Tetrahedron , vol.41 , pp. 5855
    • Pauson, P.L.1
  • 41
    • 0028109179 scopus 로고
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2085
    • Cossio, F.P.1    Arrieta, A.2    Lecea, B.3    Ugalde, J.M.4
  • 42
    • 0025734475 scopus 로고
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5784
    • Hegedus, L.S.1    Montgomery, J.2    Narukawa, Y.3    Snustad, D.C.4
  • 43
    • 0001012780 scopus 로고    scopus 로고
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 9186
    • Palomo, C.1    Aizpurua, J.M.2    Mielgo, A.3    Linden, A.4
  • 44
    • 0021076587 scopus 로고
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 2206
    • Hubschwerelen, C.1    Schmid, G.2
  • 45
    • 0027314982 scopus 로고
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 2454
    • Welch, J.T.1    Araki, K.2    Kawecki, R.3    Wichtowski, J.A.4
  • 46
    • 0001318920 scopus 로고
    • and references therein
    • The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
    • (1988) J. Org. Chem. , vol.53 , pp. 4227
    • Wagle, D.R.1    Garai, C.2    Chiang, J.3    Monteleone, M.G.4    Kurys, B.E.5    Strohmeyer, T.W.6    Hedge, V.R.7    Manhas, M.S.8    Bose, A.K.9
  • 55
    • 15144353651 scopus 로고    scopus 로고
    • note
    • 6 complexes can be isolated and characterized. See the Supporting Information for one example.
  • 56
    • 0001297245 scopus 로고
    • Examples: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396-1406. (b) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220-223.
    • (1994) J. Org. Chem. , vol.59 , pp. 1396-1406
    • Clive, D.L.J.1    Cole, D.C.2    Tao, Y.3
  • 61
    • 15144348595 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the crude reaction mixtures before purification.
  • 67
    • 0001297245 scopus 로고
    • See, for example: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396. (b) Brown, S. W.; Pauson, P. L. J. Chem. Soc., Perkin Trans. 1 1990,1205. (d) Becker, D. P.; Flynn, D. L. Tetrahedron Lett. 1993, 34, 2087. (c) Yoo, S.-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
    • (1994) J. Org. Chem. , vol.59 , pp. 1396
    • Clive, D.L.J.1    Cole, D.C.2    Tao, Y.3
  • 68
    • 37049085275 scopus 로고
    • See, for example: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396. (b) Brown, S. W.; Pauson, P. L. J. Chem. Soc., Perkin Trans. 1 1990,1205. (d) Becker, D. P.; Flynn, D. L. Tetrahedron Lett. 1993, 34, 2087. (c) Yoo, S.-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
    • (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 1205
    • Brown, S.W.1    Pauson, P.L.2
  • 69
    • 0027406256 scopus 로고
    • See, for example: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396. (b) Brown, S. W.; Pauson, P. L. J. Chem. Soc., Perkin Trans. 1 1990,1205. (d) Becker, D. P.; Flynn, D. L. Tetrahedron Lett. 1993, 34, 2087. (c) Yoo, S.-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2087
    • Becker, D.P.1    Flynn, D.L.2
  • 70
    • 0028044121 scopus 로고
    • See, for example: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396. (b) Brown, S. W.; Pauson, P. L. J. Chem. Soc., Perkin Trans. 1 1990,1205. (d) Becker, D. P.; Flynn, D. L. Tetrahedron Lett. 1993, 34, 2087. (c) Yoo, S.-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
    • (1994) J. Org. Chem. , vol.59 , pp. 6968
    • Yoo, S.-E.1    Lee, S.H.2
  • 71
    • 0000008267 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5604
    • Alcaide, B.1    Casarrubios, L.2    Domínguez, G.3    Sierra, M.A.4    Monge, A.5
  • 72
    • 33845471082 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1984) J. Org. Chem. , vol.49 , pp. 5113
    • Brouillette, W.J.1    Einspahr, H.M.2
  • 73
    • 0040409059 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 5333
    • Collins, T.J.1    Coots, R.J.2    Furutani, T.T.3    Keech, J.T.4    Peake, G.T.5    Santarsiero, B.D.6
  • 74
    • 0343953125 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 4738
    • Somayaji, V.1    Brown, R.S.2
  • 75
    • 0011222187 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1986) J. Org. Chem. , vol.51 , pp. 4866
    • Somayaji, V.1    Skorey, K.I.2    Brown, R.S.3
  • 76
    • 0006371410 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1987) J. Org. Chem. , vol.52 , pp. 805
    • Slebocka-Tilk, H.1    Brown, R.S.2
  • 77
    • 0024596054 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987,109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987,52,805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1073
    • Williams, R.M.1    Lee, B.H.2    Miller, M.M.3    Anderson, O.P.4
  • 78
    • 0001108771 scopus 로고    scopus 로고
    • Padwa, A., Eds.; Elsevier: Oxford, U.K., Chapter 1.21.3
    • Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol. 1, Chapter 1.21.3. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds-Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, pp 1-217. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. To the best of our knowledge, the sole precedent on the multistep synthesis of tricyclic azetidines and their role as serotoninergic agents is by Becker and Flynn: (d) Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1
    • De Kimpe, N.1
  • 79
    • 0002280967 scopus 로고
    • Hassner, A., Ed.; Wiley: New York
    • Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol. 1, Chapter 1.21.3. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds-Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, pp 1-217. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. To the best of our knowledge, the sole precedent on the multistep synthesis of tricyclic azetidines and their role as serotoninergic agents is by Becker and Flynn: (d) Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047.
    • (1983) Chemistry of Heterocyclic Compounds-Small Ring Heterocycles , Issue.3 PART , pp. 1-217
    • Moore, J.A.1    Ayers, R.S.2
  • 80
    • 0018726726 scopus 로고
    • Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol. 1, Chapter 1.21.3. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds-Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, pp 1-217. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. To the best of our knowledge, the sole precedent on the multistep synthesis of tricyclic azetidines and their role as serotoninergic agents is by Becker and Flynn: (d) Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047.
    • (1979) Chem. Rev. , vol.79 , pp. 331
    • Cromwell, N.H.1    Phillips, B.2
  • 81
    • 0027157468 scopus 로고
    • Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol. 1, Chapter 1.21.3. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds-Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, pp 1-217. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. To the best of our knowledge, the sole precedent on the multistep synthesis of tricyclic azetidines and their role as serotoninergic agents is by Becker and Flynn: (d) Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047.
    • (1993) Tetrahedron , vol.49 , pp. 5047
    • Becker, D.P.1    Flynn, D.L.2
  • 84
    • 0000134381 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K.
    • Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, p 685.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 685
    • Caffyn, A.J.M.1    Nicholas, K.M.2
  • 85
    • 15144346087 scopus 로고    scopus 로고
    • note
    • For clarity through this work tricyclic systems has been numbered according with the numeration used for trinems. Thus, the four-membered ring nitrogen has been assigned the locator 1 and the remaining positions have been numbered to place the higher number on the carbonyl group (for 2-azetidinones) or former carbonyl carbon (for azetidines).
  • 88
    • 0003909854 scopus 로고
    • John Wiley and Sons: Chichester. U.K.
    • Günther, H. NMR Spectroscopy; John Wiley and Sons: Chichester. U.K., 1995.
    • (1995) NMR Spectroscopy
    • Günther, H.1
  • 94
    • 0001509525 scopus 로고
    • Wiley: New York, Collect.
    • Sauer, J. C. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. IV, p 813.
    • (1993) Organic Syntheses , vol.4 , pp. 813
    • Sauer, J.C.1
  • 95
    • 15144347826 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.