Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates
King, SM; Buchwald, SL
| HERO ID | 5417840 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates |
| Authors | King, SM; Buchwald, SL |
| Journal | Organic Letters |
| Volume | 18 |
| Issue | 16 |
| Page Numbers | 4128-4131 |
| Abstract | 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. |
| Doi | 10.1021/acs.orglett.6b02082 |
| Pmid | 27498618 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |