Kinetic Resolution of Secondary Alcohols Using Connon Type Catalysts

Chiral pyridine derivatives following the general design principle proposed by Connon et al. are employed in the Lewis base mediated kinetic resolution of secondary alcohols. Variations in the size of substrates and catalyst substituents are found to impact reaction selectivity in a nonsystematic manner, while best selectivities are found for catalyst variants carrying electron‐acceptor‐substituted side chains. Solvent effects are found to be small for the most active and most selective catalysts studied, but more significant for less selective catalysts. The quantitative assessment of reaction kinetics points to a rather limited contribution of background acylation reactivity, but to a very significant temperature effect on reaction outcome.