Cinchona-based phase-transfer catalysts for asymmetric synthesis

Phase-transfer catalysis is one of the most useful methodologies for practical syntheses given its operational simplicity and mild reaction conditions that enable its application in industrial processes. Cinchona alkaloids have been a popular, natural source of practical organocatalysts due largely...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2009-01 (46), p.7090-7103
Main Authors: Jew, Sang-sup, Park, Hyeung-geun
Format: Article
Language:English
Subjects:
Catalysis
Cinchona Alkaloids - chemistry
Methods
Organic Chemicals - chemical synthesis
Organic Chemistry Phenomena
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Summary:Phase-transfer catalysis is one of the most useful methodologies for practical syntheses given its operational simplicity and mild reaction conditions that enable its application in industrial processes. Cinchona alkaloids have been a popular, natural source of practical organocatalysts due largely to their excellent commercial availability and low cost. Since the first Cinchona alkaloid-derived phase-transfer catalysts was disclosed in 1981, diverse generations of Cinchona-derived phase-transfer catalysts have been developed and successfully applied to various asymmetric syntheses. In this feature article, we describe the generation of Cinchona-derived chiral phase-transfer catalysts according to the development stages and our efforts toward the design of polymeric Cinchona phase-transfer catalysts, the effects of the electronic functional group incorporated in the catalysts, and their application in asymmetric organic reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/b914028j