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Volumn 59, Issue 49, 2003, Pages 9779-9791

On the α-lithiation-rearrangement of N-toluensulfonyl aziridines: Mechanistic and synthetic aspects

Author keywords

Aziridines; Carbenes and carbenoids; Lithiation; Rearrangement; Sulfonamides

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; AZIRIDINE DERIVATIVE; BUTYLLITHIUM; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTENE DERIVATIVE; LITHIUM DERIVATIVE; SPARTEINE; SULFONAMIDE; TOLUENESULFONAMIDE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242643405     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.024     Document Type: Article
Times cited : (48)

References (71)
  • 5
    • 0141906289 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1139
    • Hodgson, D.M.1    Stent, M.A.H.2    Stefane, B.3    Wilson, F.X.4
  • 6
    • 0037112715 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4313
    • Hodgson, D.M.1    Maxwell, C.R.2    Miles, T.J.3    Paruch, E.4    Stent, M.A.H.5    Matthews, I.R.6    Wilson, F.X.7    Witherington, J.8
  • 7
    • 85047699456 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2376
    • Hodgson, D.M.1    Gras, E.2
  • 8
    • 0034741044 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 2161
    • Hodgson, D.M.1    Cameron, I.D.2    Christlieb, M.3    Green, R.4    Lee, G.P.5    Robinson, L.A.6
  • 9
    • 0033520980 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8637
    • Hodgson, D.M.1    Robinson, L.A.2    Jones, M.L.3
  • 10
    • 0033591124 scopus 로고    scopus 로고
    • For recent examples, see: (a) Hodgson D.M., Stent M.A.H., Stefane B., Wilson F.X. Org. Biomol. Chem. 1:2003;1139 (b) Hodgson D.M., Maxwell C.R., Miles T.J., Paruch E., Stent M.A.H., Matthews I.R., Wilson F.X., Witherington J. Angew. Chem. Int. Ed. 41:2002;4313 (c) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376 (d) Hodgson D.M., Cameron I.D., Christlieb M., Green R., Lee G.P., Robinson L.A. J. Chem. Soc., Perkin Trans. 1. 2001;2161 (e) Hodgson D.M., Robinson L.A., Jones M.L. Tetrahedron Lett. 40:1999;8637 (f) Hodgson D.M., Maxwell C.R., Matthews I.R. Tetrahedron: Asymmetry. 10:1999;1847.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 1847
    • Hodgson, D.M.1    Maxwell, C.R.2    Matthews, I.R.3
  • 21
    • 0036172914 scopus 로고    scopus 로고
    • For reviews, see: (a) Eames J. Eur. J. Org. Chem. 2002;393 (b) Magnus A., Bertilsson S.K., Andersson P.G. Chem. Soc. Rev. 31:2002;223 (c) O'Brien P. J. Chem. Soc., Perkin Trans. 1. 1998;1439.
    • (2002) Eur. J. Org. Chem. , pp. 393
    • Eames, J.1
  • 22
    • 0036299781 scopus 로고    scopus 로고
    • For reviews, see: (a) Eames J. Eur. J. Org. Chem. 2002;393 (b) Magnus A., Bertilsson S.K., Andersson P.G. Chem. Soc. Rev. 31:2002;223 (c) O'Brien P. J. Chem. Soc., Perkin Trans. 1. 1998;1439.
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 223
    • Magnus, A.1    Bertilsson, S.K.2    Andersson, P.G.3
  • 23
    • 33748630800 scopus 로고    scopus 로고
    • For reviews, see: (a) Eames J. Eur. J. Org. Chem. 2002;393 (b) Magnus A., Bertilsson S.K., Andersson P.G. Chem. Soc. Rev. 31:2002;223 (c) O'Brien P. J. Chem. Soc., Perkin Trans. 1. 1998;1439.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1439
    • O'brien, P.1
  • 24
    • 0038147980 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1261
    • Johansson, A.1    Abrahamsson, P.2    Davidsson, O.3
  • 25
    • 0037459228 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 645
    • Malhotra, S.V.1
  • 26
    • 0012317165 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2002) Org. Lett. , vol.4 , pp. 3777
    • Gayet, A.1    Bertilsson, S.2    Andersson, P.G.3
  • 27
    • 0037040653 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2002) J. Org. Chem. , vol.67 , pp. 1567
    • Bertilsson, S.K.1    Södergren, M.J.2    Andersson, P.G.3
  • 28
    • 0035982105 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 1397
    • Pettersen, D.1    Amedjkouh, M.2    Nilsson Lill, S.O.3    Ahlberg, P.4
  • 29
    • 0037013848 scopus 로고    scopus 로고
    • For recent examples, see: (a) Johansson A., Abrahamsson P., Davidsson O. Tetrahedron: Asymmetry. 14:2003;1261 (b) Malhotra S.V. Tetrahedron: Asymmetry. 14:2003;645 (c) Gayet A., Bertilsson S., Andersson P.G. Org. Lett. 4:2002;3777 (d) Bertilsson S.K., Södergren M.J., Andersson P.G. J. Org. Chem. 67:2002;1567 (e) Pettersen D., Amedjkouh M., Nilsson Lill S.O., Ahlberg P. J. Chem. Soc., Perkin Trans. 1. 2002;1397 (f) Seki A., Asami M. Tetrahedron. 58:2002;4655.
    • (2002) Tetrahedron , vol.58 , pp. 4655
    • Seki, A.1    Asami, M.2
  • 30
    • 0041317374 scopus 로고    scopus 로고
    • For examples and leading references, see: (a) O'Brien P., Pilgram C.D. Org. Biomol. Chem. 1:2003;523 (b) de Sousa S.E., O'Brien P., Pilgram C.D. Tetrahedron. 58:2002;4643.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 523
    • O'brien, P.1    Pilgram, C.D.2
  • 31
    • 0037013888 scopus 로고    scopus 로고
    • For examples and leading references, see: (a) O'Brien P., Pilgram C.D. Org. Biomol. Chem. 1:2003;523 (b) de Sousa S.E., O'Brien P., Pilgram C.D. Tetrahedron. 58:2002;4643.
    • (2002) Tetrahedron , vol.58 , pp. 4643
    • De Sousa, S.E.1    O'brien, P.2    Pilgram, C.D.3
  • 42
    • 0042170072 scopus 로고    scopus 로고
    • For a preliminary communication on part of this work, see:
    • For a preliminary communication on part of this work, see: O'Brien P., Rosser C.M., Caine D. Tetrahedron Lett. 44:2003;6613.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6613
    • O'brien, P.1    Rosser, C.M.2    Caine, D.3


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