SYNTHESIS OF CHIRAL AND ACHIRAL ANALOGS OF AMBROXOL VIA PALLADIUM-CATALYZED REACTIONS

Chiral cis-and trans-4-aminocyclohex-2-enols and achiral 4-aminocycloh exanols, which all are analogues of ambroxol, are prepared via stereos elective allylic substitution of cyclohex-2-ene-1,4-diol derivatives o r 1-acetoxy-4-chlorocyclohex-2-ene. The chiral target molecules are ob tained in enantiomerically pure form by employing a previously describ ed enantiodivergent synthesis of cis-and trans-4-aminocyclohex-2-enols . It has been found that bis(amine) nucleophiles 7a and 7b react only at the benzylic amino group under the conditions employed.