Visible‐Light‐Driven Enantioselective Aerobic Oxidation of β‐Dicarbonyl Compounds Catalyzed by Cinchona‐Derived Phase Transfer Catalysts in Batch and Semi‐Flow

The direct asymmetric α‐hydroxylation of β‐dicarbonyl compounds has been developed using cinchona‐derived phase‐transfer catalysts in batch and semi‐flow processes. Using visible light as the driving force and air as oxidant, the corresponding products were obtained in excellent yields (up to 96%) a...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-11, Vol.361 (22), p.5245-5252
Main Authors: Tang, Xiao‐Fei, Zhao, Jing‐Nan, Wu, Yu‐Feng, Feng, Shi‐Hao, Yang, Fan, Yu, Zong‐Yi, Meng, Qing‐Wei
Format: Article
Language:English
Subjects:
aerobic oxidation
asymmetric catalysis
Carbonyl compounds
Enantiomers
Hydroxylation
Oxidation
Phase transfer catalysts
phase-transfer catalyst
Photosensitivity
Reaction time
semi-flow
Substrates
visible light catalysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The direct asymmetric α‐hydroxylation of β‐dicarbonyl compounds has been developed using cinchona‐derived phase‐transfer catalysts in batch and semi‐flow processes. Using visible light as the driving force and air as oxidant, the corresponding products were obtained in excellent yields (up to 96%) and good enantioselectivities (up to 90% ee). The catalyst acts as a chiral center and a catalytic center and forms a chiral enolate complex with the substrate to act as a photosensitive center in the reaction. The use of semi‐flow photochemical processes allowed a reduction in reaction time (24 h to 0.89 h) and good yields (up to 93%) and enantioselectivities (up to 88% ee) were obtained.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900777