Methyl (2Z)-2-acetamido-3-(naphthalen-2-yl)prop-2-enoate → methyl N-acetyl-3-(2-naphthyl)-D-alaninate

Participants

Reaction Steps

A solution of methyl (Z)-2acetamido-3-(2-naphthyl)propenoate (0.3 g, 1.11 mmol) and the catalyst (I) (7 mg, 0.011 mmol, 1.0 mol %) in degassed methanol (10 ml) was placed in a 50 ml Parr pressure reactor purged with nitrogen. The vessel was then purged with hydrogen (×3) and charged to 4.13 MPa (600 psi) of hydrogen. After stirring for 2 h, the solution was evaporated to give (R)-N-acetyl-3(2-naphthyl)alanine methyl ester (0.31 g, quantitative yield, 77.5% ee).

Provenance & Evidence