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Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters

Author:
Salman, Muhammad, Zhu, Zhi-Qiang, Huang, Zhi-Zhen
Source:
Organic letters 2016 v.18 no.7 pp. 1526-1529
ISSN:
1523-7052
Subject:
Lewis acids, amino acids, catalytic activity, chemical structure, copper, cross-coupling reactions, esters, oxidants, phenol
Abstract:
A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.
Agid:
5792554