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Volumn 131, Issue 6, 2009, Pages 2096-2097

Asymmetric C2-C3 cyclopentannulation of the indole ring

Author keywords

[No Author keywords available]

Indexed keywords

TUNGSTEN;

EID: 67849105019     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809919t     Document Type: Article
Times cited : (82)

References (32)
  • 2
    • 47649088268 scopus 로고    scopus 로고
    • Recently their utility as sensitizers in organic dye-sensitizer ionic liquid- based solar cells has been reported. See: Kuang, D, Uchida, S, Humphry- Baker, R, Zakeeruddin, S. M, Grätzel, M. Angew. Chem, Int. Ed 2008, 47, 1923
    • Recently their utility as sensitizers in organic dye-sensitizer ionic liquid- based solar cells has been reported. See: Kuang, D.; Uchida, S.; Humphry- Baker, R.; Zakeeruddin, S. M.; Grätzel, M. Angew. Chem., Int. Ed 2008, 47, 1923.
  • 3
    • 52049102506 scopus 로고    scopus 로고
    • For formation of the N-C7a bond, see: (a) Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452. For formation of the C3-C3a bond, see:
    • For formation of the N-C7a bond, see: (a) Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452. For formation of the C3-C3a bond, see:
  • 5
    • 48849113342 scopus 로고    scopus 로고
    • For formation of the N-C3 and N-C7a bonds, see
    • Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759. For formation of the N-C3 and N-C7a bonds, see:
    • (2008) Org. Lett , vol.10 , pp. 1759
    • Watanabe, T.1    Oishi, S.2    Fujii, N.3    Ohno, H.4
  • 6
    • 51649124289 scopus 로고    scopus 로고
    • For formation of the N-C7a and C3-C3a bonds, see
    • Minatti, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721. For formation of the N-C7a and C3-C3a bonds, see:
    • (2008) Org. Lett , vol.10 , pp. 2721
    • Minatti, A.1    Buchwald, S.L.2
  • 8
  • 20
    • 0034625892 scopus 로고    scopus 로고
    • For the catalytic asymmetric hydrogenation of substituted indoles, see
    • For the catalytic asymmetric hydrogenation of substituted indoles, see: Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 7614
    • Kuwano, R.1    Sato, K.2    Kurokawa, T.3    Karube, D.4    Ito, Y.5
  • 21
    • 33750685325 scopus 로고    scopus 로고
    • Access to enantiopure indolines has been recently accomplished by kinetic resolution. See
    • Access to enantiopure indolines has been recently accomplished by kinetic resolution. See: Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14264
    • Arp, F.O.1    Fu, G.C.2
  • 29
    • 84891747380 scopus 로고    scopus 로고
    • As one referee pointed out, a reaction pathway involving the allenyltungsten- to-propargyltungsten rearrangement followed by cyclization cannot be ruled out
    • As one referee pointed out, a reaction pathway involving the allenyltungsten- to-propargyltungsten rearrangement followed by cyclization cannot be ruled out.
  • 30
    • 84891747034 scopus 로고    scopus 로고
    • In the case of 6a, the primary fused alkoxycyclopentadiene cycloadduct was isolated prior to hydrolysis d.e. ≈ 96% by 1H NMR
    • In the case of 6a, the primary fused alkoxycyclopentadiene cycloadduct was isolated prior to hydrolysis (d.e. ≈ 96% by 1H NMR).
  • 31
    • 84891737560 scopus 로고    scopus 로고
    • The hydrolysis of cycloadduct 6b with HCl/AcOH caused cyclopropane ring cleavage, affording compound (+)-7 in 58% yield and >99% ee.
    • The hydrolysis of cycloadduct 6b with HCl/AcOH caused cyclopropane ring cleavage, affording compound (+)-7 in 58% yield and >99% ee.
  • 32
    • 84891740004 scopus 로고    scopus 로고
    • The [4, 2] cycloaddition toward 1-azadienes represents the sole precedent for these metal carbene reagents in enantioselective synthesis. See ref 18
    • The [4 + 2] cycloaddition toward 1-azadienes represents the sole precedent for these metal carbene reagents in enantioselective synthesis. See ref 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.