A planar chiral organoselenium enabled enantioselective intramolecular oxidation of trisubstituted olefins.

ABSTRACT: Electrophilic selenium catalysis has recently emerged as an attractive synthetic strategy, yet the field of enantioselective electrophilic selenium catalysis remains underdeveloped, primarily due to the scarcity of efficient chiral catalysts and limited reaction types. Herein, we disclose the design and synthesis of a series of planar chiral organoseleniums based on [2.2]paracyclophane. With these chiral organoseleniums as catalysts, we accomplish a highly enantioselective intramolecular oxidative etherification of trisubstituted olefins, providing a diverse array of optically pure chromans bearing a quaternary carbon stereocenter. The stereochemical versatility of this method enables efficient access to both product enantiomers from the same catalyst by adjusting the E/Z configurations of

SUBMITTER: Zhu W 

PROVIDER: S-EPMC12546921 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature