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Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light
Author(s) -
Lin Lu,
Bai Xiangbin,
Ye Xinyi,
Zhao Xiaowei,
Tan ChoonHong,
Jiang Zhiyong
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707899
Subject(s) - enantioselective synthesis , protonation , chemistry , catalysis , chromophore , organocatalysis , brønsted–lowry acid–base theory , photoredox catalysis , photocatalysis , covalent bond , combinatorial chemistry , visible spectrum , photochemistry , organic chemistry , materials science , ion , optoelectronics
The first catalytic asymmetric photoreduction of 1,2‐diketones and α‐keto ketimines under visible light irradiation is reported. A transition‐metal‐free synergistic catalysis platform harnessing dicyanopyrazine‐derived chromophore (DPZ) as the photoredox catalyst and a non‐covalent chiral organocatalyst is effective for these transformations. With the flexible use of a chiral Brønsted acid or base in H + transfer interchange to control the elusive enantioselective protonation, a variety of chiral α‐hydroxy ketones and α‐amino ketones were obtained with high yields and enantioselectivities.