Enantioselective Desymmetrizing Hydroalkoxylation of 1,4- and 1,8-Diynes Enabled by Chiral Brønsted Acid Catalysis
Yin Xu, Gan-Lu Qian, Da-Qiu Cui, Peng‐Cheng Qian, Chaoyue Zhao, Xin Hong, Bo Zhou, Long‐Wu Ye
Abstract
Herein, an organocatalytic enantioselective desymmetrizing hydroalkoxylation of 1,4- and 1,8-diynes is disclosed, which represents a unique chiral Brønsted acid-catalyzed desymmetrization of diynes. This protocol provides a facile and practical access to enantioenriched 1,3-diaminopropanol derivatives and γ-butyrolactones with a wide substrate scope and generally high enantioselectivities. Besides, the backbones of these products constitute the structural core of numerous bioactive molecules, and they can serve as valuable precursors for the expeditious assembly of versatile N- and O-heterocycles. Moreover, control experiments and theoretical calculations are employed to confirm the mechanistic rationale and elucidate the origin of enantioinduction.