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Stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines: highly efficient synthesis of functionalized benzazepine scaffolds.

ABSTRACT: An efficient and highly diastereoselective synthesis of 2-substituted benzo[b]azepin-5-ol via stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines has been developed. The reaction proceeds efficiently starting from versatile skeletons with mild reaction conditions as well as simple operation. Furthermore, 2-substituted benzazepinones could been obtained by simple Dess-Martin oxidation in excellent yields.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC9057913 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines: highly efficient synthesis of functionalized benzazepine scaffolds.

Zhang Yuewei Y Bao Qingqing Q Zhang Ning N Wang Shuohang S Yu Xue X

RSC advances 20201117 68

An efficient and highly diastereoselective synthesis of 2-substituted benzo[<i>b</i>]azepin-5-ol <i>via</i> stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines has been developed. The reaction proceeds efficiently starting from versatile skeletons with mild reaction conditions as well as simple operation. Furthermore, 2-substituted benzazepinones could been obtained by simple Dess-Martin oxidation in excellent yields. ...[more]

PMID: 35516537

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