Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates
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A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including methyl, tert-butyl, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experiment (DOE) analysis using JMP software. The mild reaction conditions, which use t-BuBrettPhos Pd G3 or G4 precatalyst, result in minimal racemization of the amino acid ester. This method is the first synthetic application of the t-BuBrettPhos Pd G4 precatalyst. Mechanistic studies show that the observed erosion in enantiomeric excess is due to racemization of the amino acid ester starting material and not of the product.
Date issued
2016-08Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
King, Sandra M., and Buchwald, Stephen L. “Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates.” Organic Letters 18, 16 (August 2016): 4128–4131 © 2016 American Chemical Society
Version: Final published version
ISSN
1523-7060
1523-7052