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Volumn 75, Issue 18, 2010, Pages 6312-6315

Tandem vinylogous 1,2-addition/anionic oxy-Cope reaction leading from butadiene sulfone to an orthogonally functionalized bicycle

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; FUNCTIONALIZED; MATERIALS CHEMISTRY; MEDICINAL CHEMISTRY; STEP SEQUENCES; TRANSITION STATE;

EID: 77956506356     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101389c     Document Type: Article
Times cited : (17)

References (35)
  • 10
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    • For a useful review of tandem reactions initiated by organolithium species, see
    • For a useful review of tandem reactions initiated by organolithium species, see: García, G. V.; Nudelman, N. S. Org. Prep. Proced. Int. 2003, 35, 445-500
    • (2003) Org. Prep. Proced. Int. , vol.35 , pp. 445-500
    • García, G.V.1    Nudelman, N.S.2
  • 12
    • 33751499793 scopus 로고
    • For an alternative approach to medium-sized rings from butadiene sulfone, see
    • For an alternative approach to medium-sized rings from butadiene sulfone, see: Chou, T.; Chang, C.-Y. J. Org. Chem. 1991, 56, 4560-4563
    • (1991) J. Org. Chem. , vol.56 , pp. 4560-4563
    • Chou, T.1    Chang, C.-Y.2
  • 13
    • 0029047514 scopus 로고
    • For other reports of vinylogous additions from butadiene sulfone, see
    • For other reports of vinylogous additions from butadiene sulfone, see: Chou, T.; Tseng, H.-J. Tetrahedron Lett. 1995, 36, 7105-7108
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7105-7108
    • Chou, T.1    Tseng, H.-J.2
  • 16
    • 0030866295 scopus 로고    scopus 로고
    • For reviews of the anionic oxy-Cope reaction, see
    • For reviews of the anionic oxy-Cope reaction, see: Paquette, L. A. Tetrahedron 1997, 53, 13971-14020
    • (1997) Tetrahedron , vol.53 , pp. 13971-14020
    • Paquette, L.A.1
  • 21
    • 77956498584 scopus 로고    scopus 로고
    • note
    • Treatment of 1 and 2 with LiHMDS for extended periods did not result in the direct formation of 6, suggesting that the enolate formed following the anionic oxy-Cope is not able to deprotonate the sulfone moiety.
  • 22
    • 77956508981 scopus 로고    scopus 로고
    • These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via
    • Supplementary crystallographic data for compounds 6 and 9 have been deposited with the Cambridge Crystallographic Data Centre; deposition nos. 766248 and 766249. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.
  • 23
    • 0344430089 scopus 로고    scopus 로고
    • For a similar treatment of a different system, see
    • For a similar treatment of a different system, see: White, B. H.; Snapper, M. L. J. Am. Chem. Soc. 2003, 125, 14901-14904
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14901-14904
    • White, B.H.1    Snapper, M.L.2
  • 24
    • 0001940234 scopus 로고
    • Chair-shaped transition states generally predominate in [3,3]-sigmatropic rearrangements of acyclic substrates. See: Doering, W. von E.; Roth, W. R. Tetrahedron 1962, 18, 67-74 However, conformational constraints in cyclic substrates can lead to a preference for boat-shaped transition states. See ref 8a for a more extensive discussion.
    • (1962) Tetrahedron , vol.18 , pp. 67-74
    • Doering, W.V.E.1    Roth, W.R.2
  • 25
    • 0034728122 scopus 로고    scopus 로고
    • For other examples of chelation-controlled anionic oxy-Cope reactions, see
    • For other examples of chelation-controlled anionic oxy-Cope reactions, see: Rutherford, A. P.; Hartley, R. C. Tetrahedron Lett. 2000, 41, 737-741
    • (2000) Tetrahedron Lett. , vol.41 , pp. 737-741
    • Rutherford, A.P.1    Hartley, R.C.2
  • 27
    • 0005220841 scopus 로고
    • Alkoxides become increasingly dissociated from their metal counterions moving down the series Li < Na < K. See:;, For the effect of 18-crown-6 see refs 7 and 8
    • Alkoxides become increasingly dissociated from their metal counterions moving down the series Li < Na < K. See: Msayib, K. J.; Watt, C. I. F. Chem. Soc. Rev. 1992, 21, 237-243 For the effect of 18-crown-6 see refs 7 and 8.
    • (1992) Chem. Soc. Rev. , vol.21 , pp. 237-243
    • Msayib, K.J.1    Watt, C.I.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.