biostudies-literatureZhang FNational Natural Science Foundation of ChinaShenzhen Bay Laboratory5562-5567https://www.ebi.ac.uk/biostudies/studies/S-EPMC9116300biostudies-literatureUnknown13(19)<i>cis</i>-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of <i>cis</i>-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of <i>cis</i>-hydroindole scaffolds has been realized through a chiral <i>N</i>,<i>N</i>'-dioxide/Mg(OTf)₂ complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted <i>cis</i>-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under milChemical scienceEnantioselective construction of <i>cis</i>-hydroindole scaffolds <i>via</i> an asymmetric inverse-electron-demand Diels-Alder reaction: application to the formal total synthesis of (+)-minovincine.PMC911630022001177S211101001-1S201100003Zhang FLiu YFeng XRen BTZhou YfalseEnantioselective construction of <i>cis</i>-hydroindole scaffolds <i>via</i> an asymmetric inverse-electron-demand Diels-Alder reaction: application to the formal total synthesis of (+)-minovincine.<i>cis</i>-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of <i>cis</i>-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of <i>cis</i>-hydroindole scaffolds has been realized through a chiral <i>N</i>,<i>N</i>'-dioxide/Mg(OTf)₂ complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted <i>cis</i>-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mil2022-01-01T00:00:00Z2022 May2025-04-25T18:00:14.522Z2024-11-08T13:24:36.665ZS-EPMC91163003569433710.1039/d2sc01458k