The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis

Delphine Pichon; Michele Soleilhavoup; Jennifer Morvan; Glen P. Junor; Thomas Vives; Christophe Crévisy; Vincent Lavallo; Jean-Marc Campagne; Marc Mauduit; Rodolphe Jazzar; Guy Bertrand

doi:10.1039/C9SC02810B

The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis†

Delphine Pichon,

^a Michele Soleilhavoup,

^b Jennifer Morvan,

^a Glen P. Junor,

^b Thomas Vives,

^a Christophe Crévisy,

^a Vincent Lavallo,

^b Jean-Marc Campagne,

^c Marc Mauduit,

*^a Rodolphe Jazzar

*^b and Guy Bertrand

*^b

Author affiliations

* Corresponding authors

^a Ecole Nationale Supérieure de Chimie de Rennes, Univ Rennes, CNRS, ISCR – UMR 6226, F-35000 Rennes, France
E-mail: marc.mauduit@ensc-rennes.fr

^b UCSD–CNRS Joint Research Chemistry Laboratory (UMI 3555), University of California San Diego, La Jolla, California, USA
E-mail: rjazzar@ucsd.edu, gbertrand@ucsd.edu

^c Institut Charles Gerhardt, UMR 5253 CNRS-UM2-UM1-ENSCM, 8 Rue l'Ecole Normale, 34296 Montpellier, France

Abstract

The popularity of NHCs in transition metal catalysis has prompted the development of chiral versions as electron-rich neutral stereodirecting ancillary ligands for enantioselective transformations. Herein we demonstrate that cyclic (alkyl)(amino)carbene (CAAC) ligands can also engage in asymmetric transformations, thereby expanding the toolbox of available chiral carbenes.

Chemical Science

The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis†

Abstract

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The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis

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