Asymmetric Organocatalytic Diels–Alder Reaction of Olefinic Azlactones with Unsaturated Thiazolones: Access to Spirocyclohexenone Thiazolone Skeletons

Abstract

Chiral bifunctional thiourea-catalyzed Diels-Alder reaction between olefinic azlactones and alkylidene thiazolone derivatives is reported here for the first time. The asymmetric Diels-Alder reaction delivers vicinal tertiary-quaternary stereocenters in spirocyclohexenone thiazolones in moderate to high yields and good stereochemical outcomes. The protocol can be adapted to a broad array of substrates. Moreover, the reaction is scaled up, and the chiral spirocyclohexenone thiazolone was converted into valuable spirocyclic-1,2-amidoalcohol highlighting the synthetic utility of our methodology.

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