Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp³‐Hybridized Carbon Atoms: Kinetic Resolution of β‐Amino Alcohols by p‐Methoxybenzylation

Abstract

Ac atalytic strategy was developed for asymmetric substitution reactions at sp 3 -hybridized carbon atoms by using ac hiral alkylating agent generated in situ from trichloroacetimidate and ac hiral phosphoric acid. The resulting chiral pmethoxybenzyl phosphate selectively reacts with b-amino alcohols rather than those without a b-NH functionality.T he use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.