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An Efficient Route to Polysubstituted Tetrahydronaphthols: Silver-Catalyzed [4+2] Cyclization of 2-Alkylbenzaldehydes and Alkenes

Authors

  • Prof. Dr. Shifa Zhu,

    Corresponding author
    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 (P. R. China)
    • School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 (P. R. China)
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  • Renxiao Liang,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 (P. R. China)
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  • Prof. Dr. Huanfeng Jiang,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 (P. R. China)
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  • Dr. Wanqing Wu

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 (P. R. China)
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  • We are grateful to the National Natural Science Foundation of China (Nos. 20902028 and 21172077), the Program for New Century Excellent Talents in University (NCET-10-0403), Guangdong NSF (10351064101000000), and The National Basic Research Program of China (973) (No. 2011CB808600) for financial support. This work was also supported by “The Fundamental Research Funds for the Central Universities, SCUT (No. 2012ZZ0038).”

Abstract

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Silver bullet: A methodology for stereoselective synthesis of polysubstituted tetrahydronaphthols catalyzed by [Ag+]/NPO has been developed. The reactions proceeded through an unprecedented [4+2] cyclization of 2-(2-formylphenyl)ethanone and an alkene, in both inter- and intramolecular fashion. NPO=pyridine N-oxide.

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