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  • Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates.

Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates.

Organic letters (2016-08-09)
Sandra M King, Stephen L Buchwald
要旨

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.

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製品内容

Sigma-Aldrich
tBuBrettPhos Pd G3, 96%
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XantPhos Pd G4
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rac-BINAP Pd G4
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