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Synthesis 2013; 45(6): 703-718
DOI: 10.1055/s-0032-1318154
DOI: 10.1055/s-0032-1318154
review
Guanidine Organocatalysis
Further Information
Publication History
Received: 18 December 2012
Accepted after revision: 09 January 2013
Publication Date:
18 February 2013 (online)
Abstract
An overview of the most commonly used guanidine organocatalysts and their applications in organic synthesis is presented. Privileged structures of open, monocyclic and bicyclic guanidines and guanidinium salts are showcased with prominent examples from the literature. Free guanidines have found widespread use as strong Brønsted base catalysts in asymmetric synthesis. Guanidinium salts are employed as weak Brønsted acids or hydrogen-bond-donor catalysts and chiral counterions. The nucleophilic and Lewis basic properties of guanidines are still rarely exploited, but, as of late, have been gaining increasing recognition.
1 Introduction
2 Brønsted Base Catalysis
3 Hydrogen-Bond-Donor and Brønsted Acid Catalysis
4 Lewis Base Catalysis
5 Lewis Acid Catalysis
6 Conclusion
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For selected recent reviews by other research groups, see: