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Diarylborinic Acid-Catalyzed Ring Opening of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides: Synthesis of 1,2,4-Trisubstituted Cyclopentanes

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卷 25, 期 41, 页码 7540-7544

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02886

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A diarylborinic acid-catalyzed ring opening reaction of cis-4-hydroxymethyl-1,2-cyclopentene oxides was developed, leading to the synthesis of 1,2,4-trisubstituted cyclopentane compounds containing a quaternary carbon center.
A diarylborinic acid-catalyzed ring opening of cis-4-hydroxymethyl-1,2-cyclopentene oxides was developed with N-nucleophiles including anilines, benzotriazole, and alkylamines, as well as S-nucleophiles, affording 1,2,4-trisubstituted cyclopentane compounds containing a quaternary carbon center. The mechanism study indicated that the half-cage structure formed by the epoxide substrate and the catalyst prevents the nucleophiles from attacking the inner side of the half-cage, resulting in the desired ring-opening product.

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