Synthesis 2013; 45(6): 703-718
DOI: 10.1055/s-0032-1318154
review
© Georg Thieme Verlag Stuttgart · New York

Guanidine Organocatalysis

Philipp Selig*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   eMail: philipp.selig@rwth-aachen.de
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Publikationsverlauf

Received: 18. Dezember 2012

Accepted after revision: 09. Januar 2013

Publikationsdatum:
18. Februar 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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