A Highly Efficient Approach to Chiral Homoaldols

Significance

In this report, the authors developed a potentially useful kinetic resolution of ­acetal-protected homoaldols via an intramolecular transacetalization. The resulting γ-hydroxyacetals and cyclic acetals with quaternary stereocenters were obtained with an impressive level of stereocontrol and could both be used in natural product synthesis. This work is the first example of a ­Brønsted acid catalyzed kinetic resolution, which employs transacetalization.