SYNTHESIS OF NEW CHIRAL AUXILIARIES DERIVED FROM ISOSORBIDE

Synthesis of both monobenzenesulfonates of isosorbide (1,4:3,6-dianhydrosorbitol) was regioselectively achieved in high yields via a three-step sequence. These monoesters were O-alkylated before being reacted with various primary amines to give the corresponding amino ethers. The full control of regioselectivity led either to the exo-exo or endo-endo isomers. In an independent pathway, isosorbide derived amino ethers and amino alcohols with both amino and hydroxy functions in the endo position, were synthesized from isosorbide in a four-step procedure including selective monobenzylation, tosylation, substitution by amines and debenzylation.