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Volumn 11, Issue 4, 2009, Pages 879-882

Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINATED HYDROCARBON; GLYCOSIDE; NICKEL;

EID: 62749135024     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8028737     Document Type: Article
Times cited : (91)

References (55)
  • 2
    • 29444442296 scopus 로고    scopus 로고
    • For recent reviews in C-glycoside biology, see: (a) Lin, C.-H.; Lin, H.-C.; Yang, W.-B. Curr. Toy. Med. Chem. 2005, 5, 1431.
    • For recent reviews in C-glycoside biology, see: (a) Lin, C.-H.; Lin, H.-C.; Yang, W.-B. Curr. Toy. Med. Chem. 2005, 5, 1431.
  • 16
    • 0038055611 scopus 로고    scopus 로고
    • For a leading review on transition-met al.-mediated radical reactions, see
    • For a leading review on transition-met al.-mediated radical reactions, see: Gansauer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
    • (2000) Chem. Rev , vol.100 , pp. 2771
    • Gansauer, A.1    Bluhm, H.2
  • 22
    • 0033693866 scopus 로고    scopus 로고
    • Catalytic Ni (II) /stoichiometric Mn: Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett., 2000, 1628.
    • (b) Catalytic Ni (II) /stoichiometric Mn: Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett., 2000, 1628.
  • 23
    • 37049075549 scopus 로고    scopus 로고
    • The glucosyl radical is known to adopt a boat conformation, while the mannosyl radical is a chair: (a) Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. J. Chem. Soc., Perkin Trans. 2 1986, 1453.
    • The glucosyl radical is known to adopt a boat conformation, while the mannosyl radical is a chair: (a) Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. J. Chem. Soc., Perkin Trans. 2 1986, 1453.
  • 26
    • 33847301925 scopus 로고    scopus 로고
    • For a related example of Ni-catalyzed C-alkylation, see: Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
    • For a related example of Ni-catalyzed C-alkylation, see: Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
  • 31
    • 36749022699 scopus 로고    scopus 로고
    • For examples of cross-coupling with a putative radical cyclization prior to C-C bond formation, see: (a) Phapale, V. B, Buñuel, E, García-Iglesias, M, Càrdenas, D. J. Angew. Chem, Int. Ed. 2007, 46, 8790
    • For examples of cross-coupling with a putative radical cyclization prior to C-C bond formation, see: (a) Phapale, V. B.; Buñuel, E.; García-Iglesias, M.; Càrdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790.
  • 34
    • 34447328777 scopus 로고    scopus 로고
    • For examples of SmI2-mediated C-glycoside synthesis invoking radical intermediates, see: (a) Malapelle, A, Coslovi, A, Doisneau, G, Beau, J.-M. Eur. J. Org. Chem. 2007, 3145
    • 2-mediated C-glycoside synthesis invoking radical intermediates, see: (a) Malapelle, A.; Coslovi, A.; Doisneau, G.; Beau, J.-M. Eur. J. Org. Chem. 2007, 3145.
  • 40
    • 84962339561 scopus 로고    scopus 로고
    • For mechanistic and computational studies that implicate radical intermediates in Ni-catalyzed Negishi reactions, see: (a) Lin, X, Phillips, D. L. J. Org. Chem. 2008, 73, 3680
    • For mechanistic and computational studies that implicate radical intermediates in Ni-catalyzed Negishi reactions, see: (a) Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680.
  • 42
    • 84869271931 scopus 로고    scopus 로고
    • 2 (10 mol %), ligand (15 mol %), proton source (200 mol %), DMA (0.24 M), rt, 12 h. See the Supporting Informationfor further details.
    • 2 (10 mol %), ligand (15 mol %), proton source (200 mol %), DMA (0.24 M), rt, 12 h. See the Supporting Informationfor further details.
  • 43
    • 64349104536 scopus 로고    scopus 로고
    • Subjection of glucal 3 to the standerd conditions in the presence of methyl acrylate resulted in no reaction.
    • Subjection of glucal 3 to the standerd conditions in the presence of methyl acrylate resulted in no reaction.
  • 44
    • 64349085654 scopus 로고    scopus 로고
    • The Zn-mediated reductive elimination of aceto-1-glycosyl bromides is well known from the Fischer-Zach glycal synthesis: Fischer, E.; Zach, K. Sitzungsber. Kl. Preuss. Akad. Wiss. 1913, 27, 311.
    • The Zn-mediated reductive elimination of aceto-1-glycosyl bromides is well known from the Fischer-Zach glycal synthesis: Fischer, E.; Zach, K. Sitzungsber. Kl. Preuss. Akad. Wiss. 1913, 27, 311.
  • 45
    • 64349097132 scopus 로고    scopus 로고
    • Attempts to suppress hydrolysis product 4 through the use of desiccants (molecular sieves, etc.) were unsuccessful.
    • Attempts to suppress hydrolysis product 4 through the use of desiccants (molecular sieves, etc.) were unsuccessful.
  • 46
    • 3242706187 scopus 로고    scopus 로고
    • For example, see: a
    • For example, see: (a) Liu, Y.; Gallagher, T. Org. Lett. 2004, 6, 2445.
    • (2004) Org. Lett , vol.6 , pp. 2445
    • Liu, Y.1    Gallagher, T.2
  • 48
    • 64349088987 scopus 로고    scopus 로고
    • For examples of the known difficulty in obtaining high selectivity in reactions of arabinosyl-type radicals, see refs 1 and 6d
    • For examples of the known difficulty in obtaining high selectivity in reactions of arabinosyl-type radicals, see refs 1 and 6d.
  • 49
    • 64349107289 scopus 로고    scopus 로고
    • Attempts to improve yields by using the Bn-protected glucosyl or mannosyl chlorides failed no reaction
    • Attempts to improve yields by using the Bn-protected glucosyl or mannosyl chlorides failed (no reaction).
  • 50
    • 84869271929 scopus 로고    scopus 로고
    • 1H NMR; for this reason, glucosyl bromide 27 was used thereafter.
    • 1H NMR; for this reason, glucosyl bromide 27 was used thereafter.
  • 51
    • 64349099816 scopus 로고    scopus 로고
    • The configuration of the stereocenter a to the methyl ester in the major isomer of 29 was determined by single-crystal X-ray analysis (see the Supporting Information).
    • The configuration of the stereocenter a to the methyl ester in the major isomer of 29 was determined by single-crystal X-ray analysis (see the Supporting Information).
  • 53
    • 0032491776 scopus 로고    scopus 로고
    • 2, rt, 48 h. See: Evans, D. A.; Coleman, P. J.; Carlos Dias, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738.
    • 2, rt, 48 h. See: Evans, D. A.; Coleman, P. J.; Carlos Dias, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738.
  • 54
    • 34347257749 scopus 로고    scopus 로고
    • For recent examples of Ni-catalyzed reductive coupling reactions involving transmet al.ation with dialkylzinc species, see: a
    • For recent examples of Ni-catalyzed reductive coupling reactions involving transmet al.ation with dialkylzinc species, see: (a) Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279, 1.
    • (2007) Top. Curr. Chem , vol.279 , pp. 1
    • Montgomery, J.1    Sormunen, G.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.