A highly chemo- and enantio-selective hetero-Diels–Alder reaction catalysed by chiral aluminium complexes

Abstract

A new, highly chemo- and enantio-selective catalytic hetero-Diels–Alder reaction of conjugated dienes containing allylic C–H bonds with carbonyl compounds has been developed; with the use of (S)-(–)-BINOL-AlMe (BINOL = 1,1′-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels–Alder adduct as the major product with up to 97% ee.