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Volumn 11, Issue 17, 2009, Pages 3958-3961

Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1] heptane

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; FURAN DERIVATIVE; HEPTANE; STANNOUS CHLORIDE; TIN DERIVATIVE;

EID: 69449087898     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901613k     Document Type: Article
Times cited : (19)

References (70)
  • 25
    • 0343778881 scopus 로고
    • Selected examples
    • Review: (a) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 12931316. Selected examples:
    • (1995) Chem. Rev. , vol.95 , pp. 12931316
    • Masse, C.E.1    Panek, J.S.2
  • 30
    • 0026714006 scopus 로고
    • (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599. For selected examples, see:
    • (1992) Tetrahedron , vol.48 , pp. 8545-8599
    • Postema, M.H.D.1
  • 37
    • 69449102375 scopus 로고    scopus 로고
    • See page 10881 of ref 14b
    • See page 10881 of ref 14b.
  • 38
    • 69449105738 scopus 로고    scopus 로고
    • See page 3894 of ref 13
    • See page 3894 of ref 13.
  • 39
  • 47
    • 0033757533 scopus 로고    scopus 로고
    • More substituted cases may be less selective
    • (b) More substituted cases may be less selective: Kovensky, J.; Sinay, P. Eur. J. Org. Chem. 2000, 3523-3525;
    • (2000) Eur. J. Org. Chem. , pp. 3523-3525
    • Kovensky, J.1    Sinay, P.2
  • 48
  • 49
    • 28444473884 scopus 로고    scopus 로고
    • For relevant computational studies, see
    • For relevant computational studies, see: Nokami, T.; Werz, D. B.; Seeberger, P. H. Helv. Chim. Acta 2005, 88, 2823-2831.
    • (2005) Helv. Chim. Acta , vol.88 , pp. 2823-2831
    • Nokami, T.1    Werz, D.B.2    Seeberger, P.H.3
  • 52
    • 69449086693 scopus 로고    scopus 로고
    • Enhanced reactivity of 1 suggests that the range of conditions suitable for initiation of its reactions (i.e., combinations of Lewis acids and nucleophiles) might be broader than for other types of acetals
    • Enhanced reactivity of 1 suggests that the range of conditions suitable for initiation of its reactions (i.e., combinations of Lewis acids and nucleophiles) might be broader than for other types of acetals.
  • 55
    • 69449105584 scopus 로고    scopus 로고
    • Hall reported a yield of 85% of 1 using lower pressure and mechanical stirring. See ref 20b
    • Hall reported a yield of 85% of 1 using lower pressure and mechanical stirring. See ref 20b.
  • 56
    • 0034703157 scopus 로고    scopus 로고
    • Compounds 4a, 4b, and 4e were identified by comparison to literature data, (a) 4a
    • Compounds 4a, 4b, and 4e were identified by comparison to literature data, (a) 4a: Pilli, R. A.; Riatto, V. B. Tetrahedron: Asymmetry 2000, 11, 3675-3686.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3675-3686
    • Pilli, R.A.1    Riatto, V.B.2
  • 64
    • 58149154432 scopus 로고    scopus 로고
    • For discussions of the role of ion-pairing on stereocontrol in additions to cyclic oxocarbenium ions, see: (a)
    • For discussions of the role of ion-pairing on stereocontrol in additions to cyclic oxocarbenium ions, see: (a) Krumper, J. R.; Salamant, W. A.; Woerpel, K. A. Org. Lett. 2008, 10, 4907-4910.
    • (2008) Org. Lett. , vol.10 , pp. 4907-4910
    • Krumper, J.R.1    Salamant, W.A.2    Woerpel, K.A.3
  • 67
    • 0842307518 scopus 로고    scopus 로고
    • For related mechanistic features, see: (a) Also see
    • For related mechanistic features, see: (a) Braun, M.; Kotter, W. Angew Chem., Int. Ed. 2004, 43, 514-517. Also see:
    • (2004) Angew Chem., Int. Ed. , vol.43 , pp. 514-517
    • Braun, M.1    Kotter, W.2
  • 69
    • 0030973398 scopus 로고    scopus 로고
    • 2 in the reaction of acyclic chiral acetais with allylsilane reagents, (a)
    • 2 in the reaction of acyclic chiral acetais with allylsilane reagents, (a) Matsutani, H.; Ichikawa, S.; Yaruva, J.; Kusumoto, T.; Hiyama, T. J. Am. Chem. Soc. 1997, 119, 4541-4542.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4541-4542
    • Matsutani, H.1    Ichikawa, S.2    Yaruva, J.3    Kusumoto, T.4    Hiyama, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.