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Volumn 73, Issue 7, 2008, Pages 2947-2950

Tandem addition/cyclization reaction of organozinc reagents to 2-alkynyl aldehydes: Highly efficient regio- and enantioselective synthesis of 1,3-dihydroisobenzofurans and tetrasubstituted furans

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; ENANTIOSELECTIVITY; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 41649083003     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800029m     Document Type: Article
Times cited : (40)

References (39)
  • 1
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    • 36849081349 scopus 로고    scopus 로고
    • For recent examples, see: d
    • For recent examples, see: (d) Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643.
    • (2007) J. Org. Chem , vol.72 , pp. 9643
    • Waldo, J.P.1    Larock, R.C.2
  • 21
    • 0001158063 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin
    • (c) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 911-922.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 911-922
    • Soai, K.1    Shibata, T.2
  • 22
    • 0035263817 scopus 로고    scopus 로고
    • (d) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757-824.
    • (2001) Chem. Rev , vol.101 , pp. 757-824
    • Pu, L.1    Yu, H.B.2
  • 23
    • 0242635970 scopus 로고    scopus 로고
    • (e) Pu, L. Tetrahedron 2003, 59, 9873-9886.
    • (2003) Tetrahedron , vol.59 , pp. 9873-9886
    • Pu, L.1
  • 24
    • 0035809377 scopus 로고    scopus 로고
    • For works from our group in this field, see: f
    • For works from our group in this field, see: (f) Zhao, G.; Li, X.-G.; Wang, X.-R. Tetrahedron: Asymmetry 2001, 12, 399-403.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 399-403
    • Zhao, G.1    Li, X.-G.2    Wang, X.-R.3
  • 29
    • 0008339682 scopus 로고    scopus 로고
    • An equilibrium has been proposed between a compound of 3a's type and its tautomer 2-benzylisobenzofuran; see: Smith, J. G, Wikman, R. T. J. Org. Chem. 1974, 39, 3648. However, in view of the enantioselectivity's retention during the cyclization step, such an equilibrium may be ruled out in our case
    • An equilibrium has been proposed between a compound of 3a's type and its tautomer 2-benzylisobenzofuran; see: Smith, J. G.; Wikman, R. T. J. Org. Chem. 1974, 39, 3648. However, in view of the enantioselectivity's retention during the cyclization step, such an equilibrium may be ruled out in our case.
  • 30
    • 41649119239 scopus 로고    scopus 로고
    • 2Zn in toluene at 60°C or with NaOH in THF at room temperature led to its decomposition.
    • 2Zn in toluene at 60°C or with NaOH in THF at room temperature led to its decomposition.
  • 31
    • 33744802336 scopus 로고    scopus 로고
    • For a recent review on the synthesis and uses of polysubstituted furans, see: a
    • For a recent review on the synthesis and uses of polysubstituted furans, see: (a) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076;
    • (2006) Org. Biomol. Chem , vol.4 , pp. 2076
    • Kirsch, S.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.