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

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.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [2]
  1. Ecole Nationale Supérieure de Chimie de Rennes, Univ Rennes, CNRS, F-35000 Rennes, France
  2. UCSD–CNRS Joint Research Chemistry Laboratory (UMI 3555), University of California San Diego, La Jolla, USA
  3. Institut Charles Gerhardt, UMR 5253 CNRS-UM2-UM1-ENSCM, 34296 Montpellier, France
Publication Date:
Research Org.:
Univ. of California, San Diego, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Alfred P. Sloan Foundation's University Centre for Exemplary Mentoring; National Science Foundation Graduate Research Fellowship Program; National Science Foundation (NSF)
OSTI Identifier:
1544593
Alternate Identifier(s):
OSTI ID: 1594493; OSTI ID: 1594494
Grant/Contract Number:  
SC0009376; DGE-1650112; CHE-1455348
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 10 Journal Issue: 33; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Pichon, Delphine, Soleilhavoup, Michele, Morvan, Jennifer, Junor, Glen P., Vives, Thomas, Crévisy, Christophe, Lavallo, Vincent, Campagne, Jean-Marc, Mauduit, Marc, Jazzar, Rodolphe, and Bertrand, Guy. The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis. United Kingdom: N. p., 2019. Web. https://doi.org/10.1039/C9SC02810B.
Pichon, Delphine, Soleilhavoup, Michele, Morvan, Jennifer, Junor, Glen P., Vives, Thomas, Crévisy, Christophe, Lavallo, Vincent, Campagne, Jean-Marc, Mauduit, Marc, Jazzar, Rodolphe, & Bertrand, Guy. The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis. United Kingdom. https://doi.org/10.1039/C9SC02810B
Pichon, Delphine, Soleilhavoup, Michele, Morvan, Jennifer, Junor, Glen P., Vives, Thomas, Crévisy, Christophe, Lavallo, Vincent, Campagne, Jean-Marc, Mauduit, Marc, Jazzar, Rodolphe, and Bertrand, Guy. Wed . "The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis". United Kingdom. https://doi.org/10.1039/C9SC02810B.
@article{osti_1544593,
title = {The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis},
author = {Pichon, Delphine and Soleilhavoup, Michele and Morvan, Jennifer and Junor, Glen P. and Vives, Thomas and Crévisy, Christophe and Lavallo, Vincent and Campagne, Jean-Marc and Mauduit, Marc and Jazzar, Rodolphe and Bertrand, Guy},
abstractNote = {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.},
doi = {10.1039/C9SC02810B},
journal = {Chemical Science},
number = 33,
volume = 10,
place = {United Kingdom},
year = {2019},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C9SC02810B

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Cited by: 3 works
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