Enantioselective fluorination of alpha-branched aldehydes and subsequent conversion to alpha-hydroxyacetals via stereospecific C-F bond cleavage

The highly enantioselective fluorination of alpha-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting alpha-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding alpha-hydroxyacetals in a stereospecific manner. Accordingly, the one-pot conversion of alpha-branched aldehydes into alpha-hydroxyacetals was achieved for the first time in high enantioselectivity.