Use of 1,3-oxazolidin-2-one derivatives of 3-borylpropenoic acids as β-hydroxy acrylic acid equivalents in the asymmetric Diels-Alder reaction catalyzed by a chiral titanium reagent

Abstract

Catalytic asymmetric Diels-Alder reaction was developed by employing 3-(3-boryl-propenoyl)-1,3-oxazolidin-2-one as a β-hydroxyacrylic acid equivalent. With a catalytic amount of the titanium reagent, 3-(3-borylpropenoyl)-1,3-oxazolidin-2-ones react smoothly with various dienes in the presence of Molecular Sieves 4A to afford the adducts in high yield with high optical purity. Boryl groups of the adducts were converted to hydroxyl group oxidatively.