Assignment of absolute stereochemistry to an insect pheromone by chiral amplification

Abstract

Chiral amplification, a new strategy for determining the absolute configuration of difficultly available natural secondary alcohols or analogous amines, is described. Using this technique, the R configuration can be assigned to both components of the male sex pheromone emitted by the longhorn beetle, Anaglyptus subfasciatus. The application of this approach to fourteen alcohols and four amines illustrates its scope and limitations.