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Volumn 2007, Issue 5, 2007, Pages 167-190

Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Author keywords

Asymmetric synthesis; Cycloadditions; Debenzylation; High pressure; Sulfur heterocycles

Indexed keywords


EID: 33846243270     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.514     Document Type: Article
Times cited : (14)

References (38)
  • 2
    • 13844294140 scopus 로고    scopus 로고
    • For applications of chiral sultam auxiliaries in asymmetric synthesis, see:, and references cited therein
    • For applications of chiral sultam auxiliaries in asymmetric synthesis, see: Zhang, H.-K.; Chan, W.-H.; Lee, A. W. M.; Wong, W.-Y.; Xia, P.-F. Tetrahedron: Asymmetry 2005, 16, 761 and references cited therein.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 761
    • Zhang, H.-K.1    Chan, W.-H.2    Lee, A.W.M.3    Wong, W.-Y.4    Xia, P.-F.5
  • 4
    • 0037434509 scopus 로고    scopus 로고
    • Zhuang, L.; Wai, J. S.; Embrey, M. W.; Fisher, T. E.; Egbertson, M. S.; Payne, L. S.; Guare, J. P., Jr.; Vacca, J. P.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Witmer, M. V.; Moyer, G.; Schleif, W. A.; Gabryelski, L. J.; Leonard, Y. M.; Lynch, J. J., Jr.; Michelson, S. R.; Young, S. D. J. Med. Chem. 2003, 46, 453.
    • (b) Zhuang, L.; Wai, J. S.; Embrey, M. W.; Fisher, T. E.; Egbertson, M. S.; Payne, L. S.; Guare, J. P., Jr.; Vacca, J. P.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Witmer, M. V.; Moyer, G.; Schleif, W. A.; Gabryelski, L. J.; Leonard, Y. M.; Lynch, J. J., Jr.; Michelson, S. R.; Young, S. D. J. Med. Chem. 2003, 46, 453.
  • 23
    • 85088071946 scopus 로고    scopus 로고
    • 1H- NMR integration of the crude product mixture. Only exo sultams were formed.
    • 1H- NMR integration of the crude product mixture. Only exo sultams were formed.
  • 24
    • 0037617653 scopus 로고    scopus 로고
    • For recent publications on the effect of high pressure on the diastereoselectivity of intra- and intermolecular Diels-Alder reactions, see references 4a, 4b, 4d, and: (a) Klärner, F.-G, Wurche, F. J. Prakt. Chem. 2000, 342, 609
    • For recent publications on the effect of high pressure on the diastereoselectivity of intra- and intermolecular Diels-Alder reactions, see references 4a, 4b, 4d, and: (a) Klärner, F.-G.; Wurche, F. J. Prakt. Chem. 2000, 342, 609.
  • 26
    • 85069141872 scopus 로고    scopus 로고
    • Compare transition state models depicted in reference 12
    • Compare transition state models depicted in reference 12.
  • 29
    • 0035938319 scopus 로고    scopus 로고
    • For intermolecular Diels-Alder reactions of an α,β-unsaturated N-1-phenylethyl γ-sultam with cyclopentadienes (no asymmetric induction by the chiral N-substituent observed), see: Ho, K. F.; Fung, D. C. W.; Wong, W. Y.; Chan, W. H.; Lee, A. W. M. Tetrahedron Lett. 2001, 42, 3121.
    • For intermolecular Diels-Alder reactions of an α,β-unsaturated N-1-phenylethyl γ-sultam with cyclopentadienes (no asymmetric induction by the chiral N-substituent observed), see: Ho, K. F.; Fung, D. C. W.; Wong, W. Y.; Chan, W. H.; Lee, A. W. M. Tetrahedron Lett. 2001, 42, 3121.
  • 36
    • 85088071160 scopus 로고    scopus 로고
    • 1H NMR integration of the crude product mixture. Only endo sultams were formed.
    • 1H NMR integration of the crude product mixture. Only endo sultams were formed.
  • 38
    • 85088071144 scopus 로고    scopus 로고
    • This reaction proceeds by an SN1 mechanism, since racemic 1-phenylethyl formate was isolated as the byproduct
    • N1 mechanism, since racemic 1-phenylethyl formate was isolated as the byproduct.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.