Cu-Catalyzed Cross-Electrophilic Coupling of α-Diazoesters with O-Benzoyl Hydroxylamines for the Synthesis of Unnatural N-Alkyl α-Amino Acid Derivatives
Year: 2023
Type: article
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.
Source: Organic Letters
Authors: Yiu-Wai Yeung, Chun-Ming Chan, Yu-Ting Chen, Marco Chan, Mingyu Luo, Xin Gao, Bingnan Du, Wing-Yiu Yu
Institutions: Hong Kong Polytechnic University, Nanjing Normal University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G6586781700, G8416535204
OpenAlex ID: W4317871237