Development of asymmetric cycloaddition reaction using amino alcohol and its derivative as an organocatalyst

The design of a chiral organocatalyst is very important for achievement of a high optical purity in a catalytic asymmetric reaction. Recently, we developed various chiral β-amino alcohol organocatalysts. These organocatalysts showed high levels of catalytic activity in the asymmetric Diels-Alder (DA) reactions of some dienes with dienophiles and 1,3-dipolar cycloaddition of some nitrones with α,β-unsaturated aldehydes, respectively. Especially, β-amino alcohols worked as organocatalyst in the DA reaction of 1,2-dihydropyridines with acroleins to afford the useful synthetic intermediate of Tamiflu. The review summarizes these our studies.