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Volumn 353, Issue 11-12, 2011, Pages 1927-1932

Lewis acid-mediated acetal substitution reactions: Mechanism and application to asymmetric catalysis

Author keywords

acetals; asymmetric catalysis; contact ion pair; Lewis acids; niobium; oxocarbenium ions

Indexed keywords


EID: 80052005351     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100346     Document Type: Article
Times cited : (26)

References (59)
  • 4
    • 80051987458 scopus 로고    scopus 로고
    • For examples, see
    • For examples, see
  • 21
    • 80051976050 scopus 로고    scopus 로고
    • Reactions using optically active acetals
    • Reactions using optically active acetals
  • 35
    • 80051965552 scopus 로고    scopus 로고
    • Other than those reports, there have been several papers in which oxocarbenium ions are written in schemes or figures of acetal substitution reactions. In all such cases, however, no definitive evidence of existence of the oxocarbenium ions is shown to the best of our knowledge. Moreover, it is not clear that such oxocarbenium ions are the contact ion pair or the solvated or dissociated ion pair.
    • Other than those reports, there have been several papers in which oxocarbenium ions are written in schemes or figures of acetal substitution reactions. In all such cases, however, no definitive evidence of existence of the oxocarbenium ions is shown to the best of our knowledge. Moreover, it is not clear that such oxocarbenium ions are the contact ion pair or the solvated or dissociated ion pair.
  • 36
    • 80051987803 scopus 로고    scopus 로고
    • th Annual Meeting of the Chemical Society of Japan, March 28, 2008.
    • th Annual Meeting of the Chemical Society of Japan, March 28, 2008.
  • 37
    • 80052010685 scopus 로고    scopus 로고
    • Intramolecular fashion
    • Intramolecular fashion
  • 40
    • 80052004103 scopus 로고    scopus 로고
    • Examples of intramolecular asymmetric synthesis using cyclic acetals
    • Examples of intramolecular asymmetric synthesis using cyclic acetals
  • 47
    • 23944524914 scopus 로고    scopus 로고
    • Harada et al. reported chiral boron-catalyzed enantioselective reactions of 2-substituted 1,3-dioxolanes with ketene silyl acetals.
    • T. Harada, K. Shiraishi, Synlett 2005, 1999-2002. Harada et al. reported chiral boron-catalyzed enantioselective reactions of 2-substituted 1,3-dioxolanes with ketene silyl acetals.
    • (2005) Synlett , pp. 1999-2002
    • Harada, T.1    Shiraishi, K.2
  • 49
    • 57849161638 scopus 로고    scopus 로고
    • Example of intermolecular asymmetric synthesis using acyclic acetals
    • Example of intermolecular asymmetric synthesis using acyclic acetals:, N. Umbayashi, Y. Hamashima, M. Sodeoka, Angew. Chem. 2008, 120, 4264-4267
    • (2008) Angew. Chem. , vol.120 , pp. 4264-4267
    • Umbayashi, N.1    Hamashima, Y.2    Sodeoka, M.3
  • 50
    • 53549115640 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4196-4199.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4196-4199
  • 51
    • 44949230317 scopus 로고    scopus 로고
    • Examples of intermolecular asymmetric synthesis via oxocarbenium ion, see.
    • Examples of intermolecular asymmetric synthesis via oxocarbenium ion, see, S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 7198-7199
    • Reisman, S.E.1    Doyle, A.G.2    Jacobsen, E.N.3
  • 53
  • 59
    • 80051967906 scopus 로고    scopus 로고
    • N2) on the mechanism of the reactions using a chiral Nb catalyst, because the reactions of 1 or 9 with 7 did not proceed in the presence of the Nb catalyst.
    • N2) on the mechanism of the reactions using a chiral Nb catalyst, because the reactions of 1 or 9 with 7 did not proceed in the presence of the Nb catalyst.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.