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Volumn 69, Issue 3, 2004, Pages 624-630

The First Broad Application of Alkynyl Sulfides As Dienophiles in Cobalt(I)-Catalyzed Diels-Alder Reactions

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; COBALT; OXIDATION; SULFUR COMPOUNDS;

EID: 0842285798     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0302915     Document Type: Article
Times cited : (84)

References (47)
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    • (2002) Angew. Chem. , vol.114 , pp. 1724
    • Corey, E.J.1
  • 2
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    • For recent reviews on the application of Diels-Alder reactions in total synthesis see: (a) Corey, E. J. Angew. Chem. 2002, 114, 1724; Angew. Chem., Int. Ed. 2002, 41, 1650.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1650
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    • (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. E. Angew. Chem. 2002,114, 1743; Angew. Chem., Int. Ed. 2002, 41, 1668.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1668
  • 5
    • 0002110351 scopus 로고    scopus 로고
    • For selected examples of metal-catalyzed [4+2] cycloadditions see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 7
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    • (b) tom Dieck, H.; Diercks, R. Angew. Chem. 1983, 95, 801; Angew. Chem., Int. Ed. Engl. 1983, 22, 778.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 778
  • 30
    • 0842277228 scopus 로고    scopus 로고
    • For the latest applications of our cobalt-catalyst system see: (a) Hilt, G.; Smolko, K. I. Angew. Chem. 2003, 115, 2901; Angew. Chem., Int. Ed. 2003, 43, 2795.
    • (2003) Angew. Chem. , vol.115 , pp. 2901
    • Hilt, G.1    Smolko, K.I.2
  • 31
    • 0842298941 scopus 로고    scopus 로고
    • For the latest applications of our cobalt-catalyst system see: (a) Hilt, G.; Smolko, K. I. Angew. Chem. 2003, 115, 2901; Angew. Chem., Int. Ed. 2003, 43, 2795.
    • (2003) Angew. Chem. Int. Ed. , vol.43 , pp. 2795
  • 33
    • 0842298940 scopus 로고    scopus 로고
    • note
    • 2 for the synthesis of the aryl sulfenyl chloride (Ar-SCl) overnight.
  • 34
    • 0842342017 scopus 로고    scopus 로고
    • note
    • Nitrogen-containing functional groups, even far away from the reaction center, inhibit the cycloaddition. Only recently we identified a protecting group for the nitrogen functionality (phthalimide) that allows the cycloaddition to proceed.
  • 35
    • 0037140714 scopus 로고    scopus 로고
    • 2Ph) gave 11% yield of contaminated products, while other side products were not identified. The formation of a cobalt-stabilized propargylic cation could be the rational for the low yield and the formation of the side products. For reviews concerning the Nicholas reaction see: (a) Teobald, B. J. J. Med. Chem. 2002, 58, 4133.
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    • Teobald, B.J.1
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    • note
    • A fraction containing a side product whose 1H NMR data fit to a cyclobutene derivative could be isolated in trace amounts (<2%).
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    • (a) Meier, H.; Stavridou, E.; Storek, C. Angew. Chem. 1986, 98, 838; Angew. Chem., Int. Ed. Engl. 1986, 25, 809.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.