Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 15, Pages 3740-3751Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803752
Keywords
asymmetric catalysis; chiral anions; chiral cations; organocatalysis; quaternary ammonium
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Funding
- Shenzhen STIC [JCYJ20160229205441091]
- Hong Kong RGC [16304115, 16302617, 16311616]
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Quaternary ammonium salts play an important role in asymmetric catalysis. In this Minireview, how asymmetric ion-pairing catalysis with ammonium ions has been utilized in organic synthesis is explained, particularly in the design of novel catalytic cycles. This includes the use of chiral ammonium-based catalysts for the construction of challenging stereogenic centers. Ammonium-derived electrophilic reagents, typically formed in situ and in the context of phase-transfer catalysis (PTC), have also been utilized in asymmetric bond-forming reactions. Furthermore, ammonium salts have been employed as substrates in several stereocontrolled C-N bond cleavage processes, leading to enantioenriched products by using novel asymmetric induction modes. In addition, merging ammonium ion-pairing catalysis with other catalytic approaches has also emerged as a new platform for achieving previously less straightforward reactions, thereby allowing new synthetic applications.
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