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Volumn 352, Issue 17, 2010, Pages 2881-2886

One-pot hydroxy group activation/carbon-carbon bond forming sequence using a Brønsted base/brønsted acid system

Author keywords

alkylation; electrophilic alcohols; N acyliminium; sequential organocatalysis; trichloroacetimidates

Indexed keywords


EID: 78649532766     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000602     Document Type: Article
Times cited : (40)

References (48)
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    • For a recent review on catalytic Friedel-Crafts reactions on π-alcohols, see:,. For leading references on the catalytic alkylation of active methylene derivatives, see
    • For a recent review on catalytic Friedel-Crafts reactions on π-alcohols, see:, M. Bandini, M. Tragni, Org. Biomol. Chem. 2009, 7, 1501. For leading references on the catalytic alkylation of active methylene derivatives, see
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    • For representative examples, see
    • For representative examples, see
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    • For specific examples in N,O-acetals, see
    • P. Rubenbauer, T. Bach, Tetrahedron Lett. 2008, 49, 1305. For specific examples in N,O-acetals, see
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    • 2NH (1-5mol%) catalysis
    • 2NH (1-5mol%) catalysis.
  • 14
    • 67651102874 scopus 로고    scopus 로고
    • As this work was ongoing, a Lewis acid-catalysed acylation/glycosylation sequence has been developed, see
    • As this work was ongoing, a Lewis acid-catalysed acylation/glycosylation sequence has been developed, see:, Y. Yokoyama, T. Hanamoto, K. Suzuki, K. Shimizu, H. Furuno, J. Inanaga, Heterocycles 2009, 79, 967.
    • (2009) Heterocycles , vol.79 , pp. 967
    • Yokoyama, Y.1    Hanamoto, T.2    Suzuki, K.3    Shimizu, K.4    Furuno, H.5    Inanaga, J.6
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    • in:, (Ed.: D. Horton), Academic Press: San Diego, New York pp. For a recent review, see
    • R. R. Schmidt, W. Kinzy, in: Adv. Carbohydr. Chem. Biochem., (Ed.:, D. Horton,), Academic Press: San Diego, New York, 1994; pp 21-123. For a recent review, see
    • (1994) Adv. Carbohydr. Chem. Biochem. , pp. 21-123
    • Schmidt, R.R.1    Kinzy, W.2
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    • Details are given in the Supporting Information
    • Details are given in the Supporting Information.
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    • [8a].
    • [8a].
  • 28
    • 78649553846 scopus 로고    scopus 로고
    • 2NH loading was not considered at that point
    • 2NH loading was not considered at that point.
  • 29
    • 78649533954 scopus 로고    scopus 로고
    • Recently, Dixon and co-workers reported the heterogeneous variant of such an approach with two elegant site-isolated base- and acid-catalysed cascade transformations, see
    • Recently, Dixon and co-workers reported the heterogeneous variant of such an approach with two elegant site-isolated base- and acid-catalysed cascade transformations, see
  • 34
    • 78649568406 scopus 로고    scopus 로고
    • [14] being formed (see Supporting Information)
    • [14] being formed (see Supporting Information).
  • 35
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    • 2 at room temperature
    • 2 at room temperature.
  • 36
    • 78649541643 scopus 로고    scopus 로고
    • 1HNMR and GC-MS analyses
    • 1HNMR and GC-MS analyses.
  • 37
    • 57349134538 scopus 로고    scopus 로고
    • For a recent enantioselective transformation of a trichloroacetimidate substrate catalyzed by a chiral phosphoric acid, see
    • For a recent enantioselective transformation of a trichloroacetimidate substrate catalyzed by a chiral phosphoric acid, see:, G. L. Hamilton, T. Kanai, D. F. Toste, J. Am. Chem. Soc. 2008, 130, 14984.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14984
    • Hamilton, G.L.1    Kanai, T.2    Toste, D.F.3
  • 42
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    • For the activation of acyclic N(H)-alkoxycarbonyl N,O-acetals by chiral phosphoric acids, see M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2009, 121, 2591
    • (2009) Angew. Chem. , vol.121 , pp. 2591
    • Terada, M.1    MacHioka, K.2    Sorimachi, K.3
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    • 3CN within 1h
    • 3CN within 1h.
  • 47
    • 78649625289 scopus 로고    scopus 로고
    • 3CN probably assists the cation formation, as well known in catalytic cationic chemistry
    • 3CN probably assists the cation formation, as well known in catalytic cationic chemistry.
  • 48
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    • During the preparation of this manuscript, Fairbanks and co-workers described a chiral phosphoric acid-based catalytic approach to improve the inherent stereoselectivities of glycosylations using trichloroacetimidate sugar donors
    • During the preparation of this manuscript, Fairbanks and co-workers described a chiral phosphoric acid-based catalytic approach to improve the inherent stereoselectivities of glycosylations using trichloroacetimidate sugar donors:, D. J. Cox, M. D. Smith, A. J. Fairbanks, Org. Lett. 2010, 12, 1452-1455.
    • (2010) Org. Lett. , vol.12 , pp. 1452-1455
    • Cox, D.J.1    Smith, M.D.2    Fairbanks, A.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.