Cu-Catalyzed Cross-Electrophilic Coupling of α‑Diazoesters with O‑Benzoyl Hydroxylamines for the Synthesis of Unnatural N‑Alkyl α‑Amino Acid Derivatives

We describe a Cu-catalyzed cross-electrophilic coupling reaction for synthesizing α-amino acid derivatives from α-diazoesters with O-benzoyl hydroxylamines with Cu­(OAc)2 as the catalyst and polymethylhydrosilane (PMHS) as the hydride reagent. Excellent functional group compatibilities were demonstr...

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Bibliographic Details
Published in:Organic letters 2023-02, Vol.25 (4), p.619-623
Main Authors: Yeung, Yiu-Wai, Chan, Chun-Ming, Chen, Yu-Ting, Chan, Marco, Luo, Mingyu, Gao, Xin, Du, Bingnan, Yu, Wing-Yiu
Format: Article
Language:English
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Summary:We describe a Cu-catalyzed cross-electrophilic coupling reaction for synthesizing α-amino acid derivatives from α-diazoesters with O-benzoyl hydroxylamines with Cu­(OAc)2 as the catalyst and polymethylhydrosilane (PMHS) as the hydride reagent. Excellent functional group compatibilities were demonstrated. With ethyl 2-diazo-3-oxobutanoate as the precursor, a Cu-acetoacetate complex has been characterized by ESI-MS analysis. Results from the radical trap experiments are consistent with the intermediacy of nitrogen-centered radicals. This strategy offers a simple and inexpensive synthesis of α-amino acid derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04161