A One-Pot Organometallic Route from a 4-Alkenylpyridine to a 4,4-Spiro-Linked Ethyl 1,4-Dihydropyridine-1-carboxylate

Authors

  • Gideon Fraenkel,

    Corresponding author
    1. Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)
    • Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)

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  • Albert Chow,

    1. Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)
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  • Yulan Liang,

    1. Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)
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  • Jinhua Song,

    1. Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)
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  • Judith Gallucci

    1. Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA, (phone: +1-614-292-4210; fax: +1-614-292-1685)
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Abstract

In a one-pot process without isolation of intermediates, (but-3-en-1-yl)pyridine (13) is treated sequentially with dicyclohexylborane, trimethylaluminium, and ethyl carbonochloridate yielding ethyl 1,4-dihydro-4,4-(tetramethylene)pyridine-1-carboxylate (=ethyl 8-azaspiro[4.5]deca-6,9-diene-8-carboxylate; 2) in 46% yield based on starting alkenylpyridine 13 (Scheme 5).

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