An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated α-keto esters using trans-perhydroindolic acid as a chiral organocatalyst

Article abstract of DOI:10.1002/cjoc.201200839

An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated α-keto esters was achieved by using trans-perhydroindolic acid 1d as a chiral organocatalyst with excellent asymmetric behavior. Under the optimal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield (up to 98%) for a series of β,γ-unsaturated α-keto esters. The methodology provided an efficient route to dihydropyran derivatives containing many substituent groups (including amino groups).