One-pot reactions of bicyclic zinc enolate generated from Ni-catalyzed reductive cyclization to furnish octahydro-4,7-ethanobenzofuran-9-one derivatives |
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| Authors: | Tetsuya Tsujihara Moriho Tomeba Shigeaki Ohkubo-Sato Kyoko Iwabuchi Rino Koie Natsumi Tada Satoru Tamura Tsunayoshi Takehara Takeyuki Suzuki Tomikazu Kawano |
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| Affiliation: | 1. Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan;2. Comprehensive Analysis Center, Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki 567-0047, Japan |
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| Abstract: | The one-pot reactions of catalytically generated bicyclic zinc enolate with various electrophiles are reported. The zinc enolate as a key intermediate is efficiently delivered from Ni-catalyzed reductive cyclization of alkynyl cyclohexadienone. Employing aldehydes, imine, nitroalkene, and α,β-unsaturated carbonyl compounds as electrophiles, this new class of one-pot reactions gave multi-functionalized cis-hydrobenzofurans and octahydro-4,7-ethanobenzofuran-9-one derivatives in moderate to good yields. |
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| Keywords: | Corresponding authors. One-pot reaction Reductive cyclization Cyclohexadienone Zinc enolate |
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