Stereoselective preparation of chiral compounds in Mannich-type reactions of a bicyclic imine and phenols or indole

Mannich-type reactions of a chiral bicyclic imine and various nucleophiles yield the corresponding adducts with good to high diastereoselectivity. The influence of the reaction conditions on the yield and stereochemical outcome is investigated. The configuration of the products is established by 1H NMR spectroscopy, and the major isomers of two adducts are characterized by X-ray crystallography.