Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 21, Pages 4471-4482Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201675
Keywords
TADDOLs; Chiral pool; H-bonding catalysis; Phase-transfer catalysis; Chiral Lewis bases; Asymmetric catalysis
Categories
Funding
- Austrian Science Funds (FWF) [P22508-N17]
- Austrian Science Fund (FWF) [P22508] Funding Source: Austrian Science Fund (FWF)
- Austrian Science Fund (FWF) [P 22508] Funding Source: researchfish
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Tartaric acid is one of the most prominent naturally occurring chiral compounds. Whereas its application in the production of chiral ligands for metal-catalysed reactions has been exhaustively investigated, its potential to provide new organocatalysts has been less extensively explored. Nevertheless, some impressive results, such as the use of TADDOLs as chiral H-bonding catalysts or of tartrate-derived asymmetric quaternary ammonium salt catalysts, have been reported over the last decade. The goal of this article is to provide a representative overview of the potential and the limitations of tartaric acid or TADDOLs in the creation of new organocatalysts and to highlight some of the most spectacular applications of these catalysts, as well as to summarize case studies in which other classes of chiral backbones were better suited.
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