메뉴 건너뛰기




Volumn 67, Issue 21, 2002, Pages 7283-7288

Asymmetric synthesis of 2H-azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORYLATION;

EID: 0037131238     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025995d     Document Type: Article
Times cited : (83)

References (93)
  • 3
    • 2142683508 scopus 로고    scopus 로고
    • Kates, S. A., Albericio, F., Eds.; M. Dekker: New York
    • (c) Nefti, A.; Ostresh, J. M.; Houghten, R. A. In Solid-Phase Synthesis; Kates, S. A., Albericio, F., Eds.; M. Dekker: New York, 2000; pp 617-647.
    • (2000) Solid-Phase Synthesis , pp. 617-647
    • Nefti, A.1    Ostresh, J.M.2    Houghten, R.A.3
  • 38
    • 0033569855 scopus 로고    scopus 로고
    • (a) Fields, S. F. Tetrahedron 1999, 55, 12237-12273.
    • (1999) Tetrahedron , vol.55 , pp. 12237-12273
    • Fields, S.F.1
  • 42
    • 4243950859 scopus 로고    scopus 로고
    • European Patent Application EP. 693,494, 1996
    • (e) Gonella, J.; Reiner, A. European Patent Application EP. 693,494, 1996 [Chem. Abstr. 1996,124, 261358k].
    • (1996) Chem. Abstr. , vol.124
    • Gonella, J.1    Reiner, A.2
  • 64
    • 0037149045 scopus 로고    scopus 로고
    • (b) For the asymmetric synthesis of regioisomeric mixtures of 2H-azirine-2-phosphonates and -3-phosphonates from aziridines see: Davis, F. A.; Wu, Y.; Yan, H.; Prasad, K. R.; McCoull, W. Org. Lett. 2002, 4, 655-658. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249-252.
    • (2002) Org. Lett. , vol.4 , pp. 655-658
    • Davis, F.A.1    Wu, Y.2    Yan, H.3    Prasad, K.R.4    McCoull, W.5
  • 65
    • 0033534492 scopus 로고    scopus 로고
    • (b) For the asymmetric synthesis of regioisomeric mixtures of 2H-azirine-2-phosphonates and -3-phosphonates from aziridines see: Davis, F. A.; Wu, Y.; Yan, H.; Prasad, K. R.; McCoull, W. Org. Lett. 2002, 4, 655-658. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249-252.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 249-252
    • Davis, F.A.1    McCoull, W.2
  • 66
    • 0037148993 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598. (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743. (c) Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43. (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344. (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
    • (2002) Org. Lett. , vol.4 , pp. 597-598
    • Morgan, T.1    Ray, N.C.2    Parry, D.M.3
  • 67
    • 0037169884 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598. (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743. (c) Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43. (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344. (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
    • (2002) Tetrahedron , vol.58 , pp. 1739-1743
    • Kilbrun, J.P.1    Lau, J.2    Jones, R.C.F.3
  • 68
    • 0036361380 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598. (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743. (c) Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43. (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344. (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
    • (2002) J. Comb. Chem. , vol.4 , pp. 38-43
    • Zheng, C.1    Combs, A.P.2
  • 69
    • 0035909633 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598. (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743. (c) Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43. (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344. (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
    • (2001) Org. Lett. , vol.3 , pp. 3341-3344
    • Larsen, S.D.1    Dipaolo, B.A.2
  • 70
    • 0035513451 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598. (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743. (c) Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43. (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344. (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
    • (2001) J. Comb. Chem. , vol.3 , pp. 590-597
    • Dener, J.M.1    Lease, T.G.2    Novack, A.R.3    Plunkett, M.J.4    Hocker, M.D.5    Fantauzzi, P.P.6
  • 71
    • 2142850401 scopus 로고    scopus 로고
    • note
    • Polymer-supported amines 2a and 2b are commercially available. Chiral resin-bound amines 2c,d were accomplished with use of Merrifield resin (see text and Experimental Section).
  • 72
    • 2142842722 scopus 로고    scopus 로고
    • note
    • Chiral resin-bound amines 2c,d were characterized by FTIR and elemental analyses.
  • 78
    • 2142852196 scopus 로고    scopus 로고
    • note
    • 12b
  • 83
    • 84944061052 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Eds.; Elsevier: Oxford, UK
    • (e) Hartner, F. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Eds.; Elsevier: Oxford, UK, 1996; Vol. 3, pp 261-318.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.3 , pp. 261-318
    • Hartner, F.W.1
  • 85
    • 0037016946 scopus 로고    scopus 로고
    • For recent contributions on oxazoles see: (a) Miller, R. A.; Smith, R. M.; Karady, S.; Reamer, R. A. Tetrahedron Lett. 2002, 43, 935-938. (b) Berger, R.; Shoop, W. L.; Pivnichny, J. V.; Waarmke, L. M.; Zakson-Aiken, M.; Owens, K. A.; de Montigny, P.; Schamatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T.; Coletti, S. L. Org. Lett. 2001, 3, 3715-3718. (c) Wipf, P.; Methot, J. L. Org. Lett. 2001, 3, 1261-1264.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 935-938
    • Miller, R.A.1    Smith, R.M.2    Karady, S.3    Reamer, R.A.4
  • 87
    • 0035799896 scopus 로고    scopus 로고
    • For recent contributions on oxazoles see: (a) Miller, R. A.; Smith, R. M.; Karady, S.; Reamer, R. A. Tetrahedron Lett. 2002, 43, 935-938. (b) Berger, R.; Shoop, W. L.; Pivnichny, J. V.; Waarmke, L. M.; Zakson-Aiken, M.; Owens, K. A.; de Montigny, P.; Schamatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T.; Coletti, S. L. Org. Lett. 2001, 3, 3715-3718. (c) Wipf, P.; Methot, J. L. Org. Lett. 2001, 3, 1261-1264.
    • (2001) Org. Lett. , vol.3 , pp. 1261-1264
    • Wipf, P.1    Methot, J.L.2
  • 90
    • 2142727853 scopus 로고    scopus 로고
    • note
    • 30


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.