A Simple Primary Amine Catalyst for Enantioselective α‑Hydroxylations and α‑Fluorinations of Branched Aldehydes

A new primary amine catalyst for
the asymmetric α-hydroxylation
and α-fluorination of α-branched aldehydes is described.
The products of the title transformations are generated in excellent
yields with high enantioselectivities. Both processes can be performed
within short reaction times and on gram scale. The similarity in results
obtained in both reactions, combined with computational evidence,
implies a common basis for stereoinduction and the possibility of
a general catalytic mechanism for α-functionalizations. Promising
initial results in α-amination and α-chlorination reactions
support this hypothesis.