CHIRALITY TRANSFER IN THE ESTER ENOLATE CLAISEN REARRANGEMENT OF (R)-1-METHYL-(E)-2-BUTENYL HYDROXYACETATE AND ITS APPLICATION TO THE STEREOCONTROLLED PHEROMONE SYNTHESIS

Article abstract of DOI:10.1246/cl.1984.1669

The ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2- butenyl hydroxaacetate provides complete asymmetric transfer along with 98percent erythroselectivity to give (2R,3S)-2-hydroxy-3-methyl-(E)-4-hexenoic acid.Its synthetic utility is demonstrated by the stereocontrolled synthesis of optically active pheromones.