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Volumn 11, Issue 7, 2009, Pages 1643-1646

Unusual mechanistic course of some NHC-mediated transesterifications

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBENE; DRUG DERIVATIVE; METHANE; VINYL DERIVATIVE;

EID: 64349083101     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900257t     Document Type: Article
Times cited : (24)

References (37)
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    • (b) Glorious, F. N-Heterocyclic Carbenes in Transition Met al. Catalysis. Top. Organomet. Chem. 2007, 21, 1-218.
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    • Marion, N.; Díez-Gonzalez, S.; Nolan, S. P. Ansew. Chem., Int. Ed. 2007, 46, 2988-3000.
    • (b) Marion, N.; Díez-Gonzalez, S.; Nolan, S. P. Ansew. Chem., Int. Ed. 2007, 46, 2988-3000.
  • 10
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    • For recent reviews on organocatalysis, see: a, Wiley-VCH: Weinheim
    • For recent reviews on organocatalysis, see: (a) Lelais, G; MacMllan, D. W. C. New Frontiers in Asymmetric Catalysis; Wiley-VCH: Weinheim, 2007; pp 313-358.
    • (2007) New Frontiers in Asymmetric Catalysis , pp. 313-358
    • Lelais, G.1    MacMllan, D.W.C.2
  • 12
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    • (c) List, B. Chem. Commun. 2006, 8, 819-824.
    • (2006) Chem. Commun , vol.8 , pp. 819-824
    • List, B.1
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    • Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-
    • (e) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-
  • 25
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    • For other reports on acyl-imidazolium and thiazolium species, see: a
    • For other reports on acyl-imidazolium and thiazolium species, see: (a) Davies, D. H.; Hall, J.; Smith, E. H. J. Chem. Soc., Perkin Trans.1 1989, 837-838.
    • (1989) J. Chem. Soc., Perkin Trans.1 , pp. 837-838
    • Davies, D.H.1    Hall, J.2    Smith, E.H.3
  • 29
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    • Protonated Breslow-type intermediates have been observed in NHC-mediated Baylis-Hillman reactions Hsu, J.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. 2004, 45, 4673-4676;
    • Protonated Breslow-type intermediates have been observed in NHC-mediated Baylis-Hillman reactions (Hsu, J.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. 2004, 45, 4673-4676;
  • 31
    • 34547219364 scopus 로고    scopus 로고
    • and characterized crystallographically in the NHC-mediated addition of R-hydroxypro-pargylsilanes to aldehydes: Reynolds, T. E, Stern, C. A, Scheidt, K. A. Org. Lett. 2007, 9, 2581-2584
    • and characterized crystallographically in the NHC-mediated addition of R-hydroxypro-pargylsilanes to aldehydes: Reynolds, T. E.; Stern, C. A.; Scheidt, K. A. Org. Lett. 2007, 9, 2581-2584.
  • 32
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    • Trace acet al.dehyde required to initiate this process may be fomed via an acyl-imidazolium species normally postulated. As suggested by one of the reviewers, this same acyl-imidazolium species may also be responsible for the acylation of 5 or 6, and this represents a valid variation on either pathway a or pathway b.
    • Trace acet al.dehyde required to initiate this process may be fomed via an acyl-imidazolium species normally postulated. As suggested by one of the reviewers, this same acyl-imidazolium species may also be responsible for the acylation of 5 or 6, and this represents a valid variation on either pathway a or pathway b.
  • 34
    • 64349110636 scopus 로고    scopus 로고
    • Compound 6 may also undergo O-acylation to give adduct 3 directly.
    • Compound 6 may also undergo O-acylation to give adduct 3 directly.
  • 35
    • 0012380139 scopus 로고
    • Based on the proposed mechanism of benzil rearrangement in the presence of an NHC
    • Based on the proposed mechanism of benzil rearrangement in the presence of an NHC: Lachmann, B.; Steinmaus, H.; Wanzlick, H. W. Tetrahedron 1971, 27, 4085-4090.
    • (1971) Tetrahedron , vol.27 , pp. 4085-4090
    • Lachmann, B.1    Steinmaus, H.2    Wanzlick, H.W.3
  • 37
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    • This may also be attributed to the MeOAc requiring a reaction temperature of -20 instead of -78 °C as required for vinyl acetate
    • This may also be attributed to the MeOAc requiring a reaction temperature of -20 instead of -78 °C as required for vinyl acetate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.