Asymmetric Methanolysis of Cyclic meso-Anhydrides with Tripodal 2,6-trans-1,2,6-Trisubstituted Piperidine as Chiral Amine Catalyst

Abstract

An optically active tripodal amine, (2S,6S)-2,6-bis(o-hydroxyphenyl)-1-(2- pyridylmethyl)piperidine, was proven to be a potent chiral catalyst (1-5 mol%) for methanolytic asymmetric desymmetrization of cyclic meso-anhydrides to hemiesters. A good level of enantioselectivities (up to 81% ee) was achieved for various substrates, some of which were reported to be poor substrates for methanolysis using known chiral amines as catalysts. © Georg Thieme Verlag Stuttgart.