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Volumn 70, Issue 24, 2005, Pages 10096-10098

Silver(I)-catalyzed novel cascade cyclization reactions: Incorporation of allenes into the isochromenes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERS; POSITIVE IONS; SILVER; SYNTHESIS (CHEMICAL);

EID: 28044438949     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051524q     Document Type: Article
Times cited : (68)

References (57)
  • 27
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    • (n) Ma, S. Chem. Rev. 2005, 105, 2829-2871.
    • (2005) Chem. Rev. , vol.105 , pp. 2829-2871
    • Ma, S.1
  • 34
    • 3543001648 scopus 로고    scopus 로고
    • (a) Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139-5142. For other reports on synthesis of the cyclic alkenyl ethers, see:
    • (2004) J. Org. Chem. , vol.69 , pp. 5139-5142
    • Patil, N.T.1    Yamamoto, Y.2
  • 41
    • 24944453027 scopus 로고    scopus 로고
    • (b) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679-7685. For homogeneous gold-catalyzed reactions, see also:
    • (2005) J. Org. Chem. , vol.70 , pp. 7679-7685
    • Yao, T.1    Zhang, X.2    Larock, R.C.3
  • 43
    • 22144452177 scopus 로고    scopus 로고
    • and references therein
    • Silver(I) salts acts as a Lewis acid as well as a transition metal catalyst. See: Yao, X.; Li C.-J. J. Org. Chem. 2005, 70, 5752-5755 and references therein.
    • (2005) J. Org. Chem. , vol.70 , pp. 5752-5755
    • Yao, X.1    Li, C.-J.2
  • 44
    • 26444461420 scopus 로고    scopus 로고
    • The reason for the failure of reaction in the case of terminal alkynes (R = H) and TMS (R = TMS)-protected alkynes can be well accounted. The reaction of terminal alkynes with Ag(I) salts would lead to the formation of silver acetylide, thereby hampering the cyclization. See: Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395-4398. However, in the TMS-protected alkynes, steric hindrance created by three methyl groups might hamper the cyclization.
    • (2005) Org. Lett. , vol.7 , pp. 4395-4398
    • Yao, X.1    Li, C.-J.2
  • 45
    • 0032817852 scopus 로고    scopus 로고
    • The intramolecular 5-exo-dig/6-endo-dig cyclization of oxygen nucleophiles to alkynes has been reported. See, for instance: (a) Sashida, H.; Kawamukai, A. Synthesis 1999, 1145-1148.
    • (1999) Synthesis , pp. 1145-1148
    • Sashida, H.1    Kawamukai, A.2
  • 48
    • 0037202125 scopus 로고    scopus 로고
    • Such type of transition metal-catalyzed benzopyrylium cation formation is known in the case of the compounds containing alkynes tethered with carbonyl groups. See: (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650-12651.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12650-12651
    • Asao, N.1    Takahashi, K.2    Lee, S.3    Kasahara, T.4    Yamamoto, Y.5
  • 55
    • 0037129388 scopus 로고    scopus 로고
    • Aza-Michael reaction of enones catalyzed by transition metal salts are known. See: Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
    • (2002) Org. Lett. , vol.4 , pp. 1319-1322
    • Kobayashi, S.1    Kakumoto, K.2    Sugiura, M.3
  • 56
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    • note
    • 1H NMR analysis. (Diagram presented)
  • 57
    • 28044455062 scopus 로고    scopus 로고
    • note
    • 6).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.