메뉴 건너뛰기




Volumn , Issue 11, 2007, Pages 1790-1794

Golden opportunities in stereoselective catalysis: Optimization of chirality transfer and catalyst efficiency in the gold-catalyzed cycloisomerization of α-hydroxyallenes to 2,5-dihydrofurans

Author keywords

Allenes; Chirality transfer; Cycloisomerization; Gold catalysis; Heterocycles

Indexed keywords

2,2' BIPYRIDINE; 2,5 DIHYDROFURAN DERIVATIVE; ACETONITRILE; ALLENE DERIVATIVE; ALPHA HYDROXYALLENE DERIVATIVE; BETA HYDROXYALLENE DERIVATIVE; FURAN DERIVATIVE; GOLD; GOLD CHLORIDE; UNCLASSIFIED DRUG;

EID: 34447499044     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982561     Document Type: Article
Times cited : (95)

References (50)
  • 4
    • 34447527729 scopus 로고    scopus 로고
    • 936, and references cited therein
    • Angew. Chem. 2000, 112, 936, and references cited therein.
    • (2000) Angew. Chem , vol.112
  • 6
    • 34447499002 scopus 로고    scopus 로고
    • 3237, and references cited therein
    • Angew. Chem. 2004, 116, 3237, and references cited therein.
    • (2004) Angew. Chem , vol.116
  • 25
    • 2442559990 scopus 로고    scopus 로고
    • Recent reviews on gold catalysis in organic synthesis: a
    • Recent reviews on gold catalysis in organic synthesis: (a) Arcadi, A.; Giuseppe, S. D. Curr. Org. Chem. 2004, 8, 795.
    • (2004) Curr. Org. Chem , vol.8 , pp. 795
    • Arcadi, A.1    Giuseppe, S.D.2
  • 28
    • 84906441311 scopus 로고    scopus 로고
    • Crabtree, R. H, Mingos, D. M. P, Eds, Elsevier: Oxford
    • (d) Krause, N.; Morita, N. In Comprehensive Organometallic Chemistry III, Vol. 9; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Oxford, 2006, 501-586.
    • (2006) Comprehensive Organometallic Chemistry III , vol.9 , pp. 501-586
    • Krause, N.1    Morita, N.2
  • 30
    • 34249789370 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 8064.
    • (2006) Chem , vol.118 , pp. 8064
    • Angew1
  • 37
    • 33947724910 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 1930.
    • (2006) Chem , vol.118 , pp. 1930
    • Angew1
  • 38
    • 33746048429 scopus 로고    scopus 로고
    • In the presence of gold catalysts, γ- or δ-heterosubstituted allenes also provide five- or six-membered heterocycles (by exo-cyclization, a) Zhang, Z, Liu, C, Kinder, R. E, Han, X, Qian, H, Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066
    • In the presence of gold catalysts, γ- or δ-heterosubstituted allenes also provide five- or six-membered heterocycles (by exo-cyclization): (a) Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
  • 40
    • 34447514336 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 287.
    • (2007) Chem , vol.119 , pp. 287
    • Angew1
  • 43
    • 34447527727 scopus 로고    scopus 로고
    • No reaction takes place if substrate 1 is treated with small amounts of coned HCl alone.
    • No reaction takes place if substrate 1 is treated with small amounts of coned HCl alone.
  • 44
    • 33645059154 scopus 로고    scopus 로고
    • For an in situ reduction of gold(III) during the cyclization of an α-hydroxyallene, see: Hashmi, A. S. K.; Blanco, M. C.; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
    • For an in situ reduction of gold(III) during the cyclization of an α-hydroxyallene, see: Hashmi, A. S. K.; Blanco, M. C.; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
  • 49
    • 34447526726 scopus 로고
    • The substrates are 1: mixtures of diastereomers with regard to the 'acyclic' hydroxy group
    • Angew. Chem. 2007, 119, 1677. The substrates are 1:1 mixtures of diastereomers with regard to the 'acyclic' hydroxy group.
    • (1677) Angew. Chem , vol.119 , pp. 1
  • 50
    • 34447544526 scopus 로고    scopus 로고
    • Representative Procedure and Spectroscopic Data, Synthesis of cis-2-(tert-Butyldimethylsilyloxy)-3-methyl- 5-phenyl-2,5-dihydrofuran (2) To a solution of 1-(tert- butyldimethylsilyloxy)-3-methyl-5-phenylpenta-3,4-dien-2-ol (1, 80 mg, 0.26 mmol) and 2,2′-bipyridine (2.0 mg, 12.8 μmol) in 3 mL of dry CH 2Cl2 was added AuCl3 (2.0 mg, 6.6 μmol, After stirring for 1 h at r.t, the solvent was evaporated, and the residue was purified by column chromatography (SiO2, EtOAc-cyclohexane, 1:10) furnishing 56 mg (70, of the 2,5-dihydrofuran 2 as a slightly yellow oil (dr > 97:3 according to NMR analysis, 1H NMR (400 MHz, C 6D6, δ, 7.50 (d, 3JJ HH, 7.5 Hz, 2 H, 7.29 (m, 2 H, 7.18 (m, 1 H, 5.79 (m, 1 H, 5.34 (m, 1 H, 4.77 (m, 1 H, 3.86 dd, 2JHH, 10.6 Hz, 3J
    • 3): δ = 142.3, 137.4, 128.1, 127.5, 126.9, 125.4, 88.5, 86.7, 65.2, 25.8, 18.3, 12.6, -5.5, -5.6 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.