Affiliation:
1. Department of Chemistry Faculty of Science Hokkaido University Kita 10 Nishi 8 Kita-ku, Sapporo Hokkaido 060-0810 Japan
2. Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University Kita 21 Nishi 10 Kita-ku, Sapporo Hokkaido 001-0021 Japan
Abstract
AbstractHydrocarboxylation of methyl 2‐octynoate, a chemical commercially available at a low cost, with N‐protected amino acids was developed with a gold‐zinc cooperative catalyst constructed with a 5‐[(2,2′‐bipyridin)‐5‐yl]imidazo[1,5‐a]pyridin‐3‐ylidene to prepare α‐methoxycarbonyl enol esters as acylating reagents. The α‐methoxycarbonyl enol esters were isolable through silica‐gel column chromatography and storable without precautions regarding moisture. Acylation of free amines with the α‐methoxycarbonyl enol esters proceeded without epimerization of the stereogenic center derived from the enol esters, affording analytically pure dipeptide compounds through filtration and hexane‐washing.
Funder
Akiyama Life Science Foundation