Imidolactones, IV: N-(2-Phenylethyl)-hexahydroisochromane-1-imines

Article abstract of DOI:10.1002/ardp.19893220913

The aminolysis of cis-hexahydroisochromane-2-one (cis-2) with the 2-phenylethylamines 1 can be regulated in such a way that mainly the cis- or mainly the trans-δ-hydroxyamides 3 result.These compounds react with SOCl2 to the corresponding isochromane-1-imines 4 (not isolable in our case), the structure of which is proofed by hydrolysis to 1 and 2, as well as by preparative reaction to the δ-chloroamides 5 and by reduction to the δ-aminoalcoholes 6.All reactions of 3 and of 4 proceed with retention of the configuration.