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Volumn 64, Issue 26, 1999, Pages 9521-9528

[2 + 1] cycloaddition reactions of a 1-seleno-2-silylethene to 2- sulfonylacrylates: Stereoselective synthesis of sulfone-substituted cyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

1 SELENO 2 SILYLETHENE DERIVATIVE; 2 SULFONYLACRYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; ORGANOSULFUR DERIVATIVE; SULFONE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0033601283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9911591     Document Type: Article
Times cited : (17)

References (46)
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    • For sulfur-containing biologically interesting cyclopropanes, see: (a) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (b) Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel. E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994,59, 1243. Clerici, F.; Gelmi, M. L.; Pocar, D. J. Org. Chem. 1999, 64, 726. Nakamura, H.; Ohtoshi, M.; Sampei, O.; Akashi, Y.; Murai, A. Tetrahedron Lett. 1992, 33, 2821.
    • (1995) Curr. Med. Chem. , vol.2 , pp. 511
    • Salaün, J.1    Baird, M.S.2
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    • For sulfur-containing biologically interesting cyclopropanes, see: (a) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (b) Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel. E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994,59, 1243. Clerici, F.; Gelmi, M. L.; Pocar, D. J. Org. Chem. 1999, 64, 726. Nakamura, H.; Ohtoshi, M.; Sampei, O.; Akashi, Y.; Murai, A. Tetrahedron Lett. 1992, 33, 2821.
    • (1994) J. Org. Chem. , vol.59 , pp. 1243
    • Gerwick, W.H.1    Proteau, P.J.2    Nagle, D.G.3    Hamel, E.4    Blokhin, A.5    Slate, D.L.6
  • 23
    • 0033525032 scopus 로고    scopus 로고
    • For sulfur-containing biologically interesting cyclopropanes, see: (a) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (b) Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel. E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994,59, 1243. Clerici, F.; Gelmi, M. L.; Pocar, D. J. Org. Chem. 1999, 64, 726. Nakamura, H.; Ohtoshi, M.; Sampei, O.; Akashi, Y.; Murai, A. Tetrahedron Lett. 1992, 33, 2821.
    • (1999) J. Org. Chem. , vol.64 , pp. 726
    • Clerici, F.1    Gelmi, M.L.2    Pocar, D.3
  • 24
    • 0026747203 scopus 로고
    • For sulfur-containing biologically interesting cyclopropanes, see: (a) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (b) Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel. E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994,59, 1243. Clerici, F.; Gelmi, M. L.; Pocar, D. J. Org. Chem. 1999, 64, 726. Nakamura, H.; Ohtoshi, M.; Sampei, O.; Akashi, Y.; Murai, A. Tetrahedron Lett. 1992, 33, 2821.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2821
    • Nakamura, H.1    Ohtoshi, M.2    Sampei, O.3    Akashi, Y.4    Murai, A.5
  • 30
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    • (a) Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685. In the following references methyl 2-(phenylsulfonyl)acrylate appears; however, the preparation was not described.
    • (1983) J. Org. Chem. , vol.48 , pp. 3685
    • Snider, B.B.1    Phillips, G.B.2
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    • note
    • 2).
  • 35
    • 0343081346 scopus 로고    scopus 로고
    • note
    • 1H NMR of the reaction mixture. Due to instability to column chromatography, the mixture could not be isolated.
  • 42
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    • note
    • 3
  • 43
    • 0343517415 scopus 로고    scopus 로고
    • note
    • 4 coordination to 3a possibly gives rise to a highly enhanced reactivity in the synclinal addition. The calculation results and the discussion are presented in the Supporting Information.
  • 46
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    • Harrison, R. G., Ed.; Blackie: Glasgow
    • For examples of chlorine-bridged tin(IV) complexes and 4-8 coordinated tin(IV) complexes, see: Harrison, R. G. In Chemistry of Tin; Harrison, R. G., Ed.; Blackie: Glasgow, 1989; p 9.
    • (1989) Chemistry of Tin , pp. 9
    • Harrison, R.G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.