Enantioselective construction of cis-hydroindole scaffolds via an asymmetric inverse-electron-demand Diels-Alder reaction: application to the formal total synthesis of (+)-minovincine.

ABSTRACT: cis-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 cis-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis-hydroindole scaffolds has been realized through a chiral N,N'-dioxide/Mg(OTf)₂ complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis-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 mil

SUBMITTER: Zhang F 

PROVIDER: S-EPMC9116300 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature