High-pressure and thermally induced asymmetric Diels-Alder cycloadditions of heterosubstituted dienes to homochiral α,β-didehydro amino acid derivatives

An amino pentenoate and an unsaturated oxazolone have shown to be suitable homochiral dienophiles to be reacted with electron-rich heterosubstituted dienes. High-pressure and thermal activation have been studied for these cycloadditions. The adducts obtained are polyfunctional building blocks useful for the synthesis of enantiopure cyclohexane amino acids and related products.