‘Transmitted’ remote double diastereoselection effects on the asymmetric reduction of β-boronate oxime ethers

Remote asymmetric induction in the reduction of a homochiral β-boronate oxime ether to the corresponding amine failed to provide asymmetric induction with achiral reducing agents, but use of a chiral reducing agent produced extreme double diastereoselection effects which show that remote asymmetry can be ‘transmitted’ by suitable choice of a ‘partner’ molecule.