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One-pot reactions of bicyclic zinc enolate generated from Ni-catalyzed reductive cyclization to furnish octahydro-4,7-ethanobenzofuran-9-one derivatives
Authors:Tetsuya Tsujihara  Moriho Tomeba  Shigeaki Ohkubo-Sato  Kyoko Iwabuchi  Rino Koie  Natsumi Tada  Satoru Tamura  Tsunayoshi Takehara  Takeyuki Suzuki  Tomikazu Kawano
Institution: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
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.
Keywords:Corresponding authors    One-pot reaction  Reductive cyclization  Cyclohexadienone  Zinc enolate
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