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

Yiu Wai Yeung, Chun Ming Chan, Yu Ting Chen, Marco Chan, Mingyu Luo, Xin Gao, Bingnan Du, Wing Yiu Yu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)619-623
Number of pages5
JournalOrganic Letters
Volume25
Issue number4
DOIs
Publication statusPublished - 3 Feb 2023

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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