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Volumn 7, Issue 4, 2005, Pages 533-536

Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2′-amino)-β-lactams

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AZIDE; BETA LACTAM DERIVATIVE;

EID: 14844339773     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047815n     Document Type: Article
Times cited : (39)

References (36)
  • 1
    • 49149145492 scopus 로고    scopus 로고
    • For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
    • (1980) Tetrahedron , vol.36 , pp. 1901-1930
    • Magid, R.M.1
  • 2
    • 0001391794 scopus 로고
    • For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
    • (1980) Tetrahedron , vol.36 , pp. 2809-2931
    • Toromanoff, E.1
  • 3
    • 0026738593 scopus 로고
    • For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
    • (1992) Tetrahedron , vol.48 , pp. 7383-7423
    • Paquette, L.A.1    Stirling, C.J.M.2
  • 4
    • 49149145492 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, Chapter 24
    • For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
    • (1999) Comprehensive Asymmetric Catalysis II , pp. 833-884
    • Pfaltz, A.1    Lautens, M.2
  • 5
    • 0042379988 scopus 로고    scopus 로고
    • For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
    • (2003) Chem. Rev. , vol.103 , pp. 2921-2943
    • Trost, B.M.1    Crawley, M.L.2
  • 16
    • 0016711763 scopus 로고
    • For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
    • (1975) J. Org. Chem. , vol.40 , pp. 3491-3496
    • Lee, D.L.1    Rapoport, H.2
  • 17
    • 0022553256 scopus 로고
    • For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
    • (1986) Tetrahedron , vol.42 , pp. 3097-3110
    • Baldwin, J.E.1    Otsuka, M.2    Wallace, P.M.3
  • 18
    • 0024557406 scopus 로고
    • For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
    • (1989) J. Med. Chem. , vol.32 , pp. 165-170
    • Greenlee, W.J.1    Springer, J.P.2    Patchett, A.A.3
  • 31
    • 14844341865 scopus 로고    scopus 로고
    • note
    • Reaction of 1a carried out at rt afforded, in about 70 h, (E)-2a as the major isomer (56%), (Z)-3a (29%), and 4a (15%).
  • 32
    • 14844340236 scopus 로고    scopus 로고
    • note
    • 1H NMR signal of H1′ resonating at 5.0 ppm; see Supporting Information.
  • 35
    • 14844366674 scopus 로고    scopus 로고
    • note
    • 2 = 1.037.
  • 36
    • 14844365877 scopus 로고    scopus 로고
    • note
    • 3 (c 1.0); Chiralcel OD (Daicel column), cellulose tris(3,5-dimethyl-phenyl)carbamate phase coated on 10 μm silica gel, n-hexane/2-propanol 90:10 solvent mixture, flow 0.5 mL/min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.