Iron<sup>III</sup>-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins
Tangyu Zhan, Liang Zhou, Yuqiao Zhou, Bingqian Yang, Xiaoming Feng, Xiaohua Liu
Abstract
formation of cationic species, this method yields a range of bicyclic dihydropyran derivatives with exceptional outcomes, including high yields (up to 99%), diastereoselectivity (up to 99 : 1) and enantioselectivity (up to 99% ee) under mild conditions. This facile protocol was available for the late-stage modification of several bioactive molecules and transformation into macrocycle molecules as well. The origins of enantioselectivity were elucidated based on control experiments.
Topics & Concepts
DihydropyranChemistryCationic polymerizationCatalysisHOMO/LUMOLewis acids and basesLewis acid catalysisMoleculeDiels–Alder reactionFerricCombinatorial chemistryOrganic chemistryMedicinal chemistrySynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisOxidative Organic Chemistry Reactions