Formal Nitrene Insertion into the β‑Vinyl C–H Bond of Acroleins: Synthesis of Enaminals

An efficient formal nitrene insertion reaction into the β-vinyl C–H bond of acroleins with an electron-rich organic azide was developed. The reaction protocol can produce secondary enaminals in high yield with a broad substrate scope. In the reaction, acid mediated [3 + 2] cycloaddition of organic a...

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Bibliographic Details
Published in:Organic letters 2023-01, Vol.25 (1), p.179-183
Main Authors: Zhang, Dongsheng, Zheng, Huatao, Zeng, Lei, Nie, Yi, Fan, Yingzhu, Rao, Weidong, Gao, Lizhu
Format: Article
Language:English
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Summary:An efficient formal nitrene insertion reaction into the β-vinyl C–H bond of acroleins with an electron-rich organic azide was developed. The reaction protocol can produce secondary enaminals in high yield with a broad substrate scope. In the reaction, acid mediated [3 + 2] cycloaddition of organic azides with an acrolein generated intermediate protonated triazolines, which were selectively decomposed into enaminals with addition of a weakly Brønsted basic reagent such as methanol. The resulting secondary enaminal could be easily reduced into a γ-amino alcohol under mild hydrogenation conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04028