Abstract
Asymmetric phase-transfer catalysis has been widely applied into organic synthesis for efficiently creating chiral functional molecules. In the past decades, chiral phase-transfer catalysts with proton donating groups are emerging as an extremely significant strategy in the design of novel catalysts, and a large number of enantioselective reactions have been developed. In particular, the proton donating groups including phenol, amide, and (thio)-urea exhibited unique properties for cooperating with the phase-transfer catalysts, and great advances on this field have been made in the past few years. This review summarizes the seminal works on the design, synthesis, and applications of chiral phase-transfer catalysts with strong hydrogen bonding interactions.
Highlights
Since Starks firstly introduced the term “phase-transfer catalysis” in 1971 [1], it has been widely applied in organic reactions in different immiscible phases
The phase-transfer catalysts that are based on the skeletons of cinchona alkaloids, and chiral binaphthyls were emerging as the most successful examples, including the quaternary ammonium salts and quaternary phosphonium salts (Scheme 1a) [3,4,5,6,7,8,9,10,11,12,13,14]
Inspired by the bifunctional Brønsted bases with proton donating groups, which have been successfully applied into building chiral compounds over the past decades, chiral phase transfer catalysts with hydrogen donating groups have got attained attentions from chemists
Summary
Since Starks firstly introduced the term “phase-transfer catalysis” in 1971 [1], it has been widely applied in organic reactions in different immiscible phases. As a significant interaction force, widely exists in biomacromolecules, such as proteins and nucleic acids, which was successfully applied in the design and synthesis of novel catalysts, especially for the organocatalysts [16] It has attracted chemists’ attention in the design of efficient phase-transfer catalysts, which has become a hot topic, especially in the past few years (Scheme 1b). This review will cover the design, synthesis, and applications of chiral phase-transfer catalysts with proton donating groups in order to accelerate the development of this area. Palomo and co-workers interpreted thethe importance of the hydrogen bond based on the mechanistic significant role in improving enantioselectivities of these organic reactions.
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