Diastereoselective carboxyl migrations of 3-arylbenzofuranones.
Mixed benzofuranyl carbonates derived from chiral chloroformates rearranged in the presence of nucleophilic catalysts to give C-carboxylated benzofurans with variable dr. The use of chiral nucleophilic catalysts gave modest improvement in dr, but better results were obtained by optimizing auxiliary and catalyst. Thus, 8k was obtained with 9:1 dr.
Peris
Gorka
G
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA. gorka.peris@yale.edu
Vedejs
Edwin
E
D001572:Benzofurans / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001572:Benzofurans; D002264:Carboxylic Acids