Jump to main content
Jump to site search


Chiral guanidines and their derivatives in asymmetric synthesis

Author affiliations

Abstract

Over the past two decades, chiral guanidines and their derivatives have emerged as one of the most powerful organocatalysts mainly on the basis of their strong basicity and/or hydrogen-bond donor ability. Structurally diverse guanidine catalysts (bicyclic, monocyclic and acyclic types) sprang up and enabled numerous fundamental organic transformations to be realized in high efficiency and stereoselectivity. Moreover, chiral guanidinium salts were successfully employed in H-bond donor catalysis, phase-transfer catalysis and others. Recently, several novel chiral guanidine derivatives [e.g., guanidinium salt, pentanidium, bis(guanidino)iminophosphorane] have been designed and used for the synthesis of valuable molecules. In addition, the combination of chiral guanidines and their derivatives with cationic or anionic metal species dramatically expanded their utility and provided solutions to challenging transformations of importance which cannot be achieved with conventional chiral catalysts. This article reviews current achievements of chiral guanidines and their derivatives in organocatalysis, and updates versatile guanidine–metal salt combinations in asymmetric catalytic reactions. In addition, representative examples of achiral guanidine-related catalysis are also covered.

Graphical abstract: Chiral guanidines and their derivatives in asymmetric synthesis

Back to tab navigation

Publication details

The article was received on 30 May 2018 and first published on 30 Oct 2018


Article type: Tutorial Review
DOI: 10.1039/C7CS00792B
Citation: Chem. Soc. Rev., 2018, Advance Article
  •   Request permissions

    Chiral guanidines and their derivatives in asymmetric synthesis

    S. Dong, X. Feng and X. Liu, Chem. Soc. Rev., 2018, Advance Article , DOI: 10.1039/C7CS00792B

Search articles by author

Spotlight

Advertisements