Design of primary amine-functionalized polymer containing chiral isosorbide in the main chain for the asymmetric synthesis of isoquinuclidine derivatives

Abstract

The present article is concerned with the synthesis, characterization, and application of a novel amine-functionalized optically active polymer consisting of isosorbide units attached in the main chain. This polymer could be used as a chiral homogeneous organocatalyst for the one-pot three component asymmetric synthesis of isoquinuclidine derivatives via aza-Diels–Alder reaction. Recyclability, the use of a low amount of catalyst, simple work up procedure, excellent diastereoselectivity, moderate enantioselectivity, and high yield of products make the isosorbide containing primary amine-functionalized chiral polymer (Chiral-ISO-PECH-Amine), a potential catalyst for the synthesis of isoquinuclidine derivatives.