Synthesis 2014; 46(02): 242-250
DOI: 10.1055/s-0033-1340215
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Characterization of New Chiral Azolinium Salts, Precursors to N-Heterocyclic Carbenes, Derived from l-Proline

Amélia Thomasset
a   Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud, 91405 Orsay Cedex, France   eMail: giang.vo-thanh@u-psud.fr
,
Lucie Bouchardy
a   Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud, 91405 Orsay Cedex, France   eMail: giang.vo-thanh@u-psud.fr
,
Chloée Bournaud
a   Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud, 91405 Orsay Cedex, France   eMail: giang.vo-thanh@u-psud.fr
,
Régis Guillot
b   CNRS, Délégation Ile de France Sud, Orsay, France
,
Martial Toffano
a   Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud, 91405 Orsay Cedex, France   eMail: giang.vo-thanh@u-psud.fr
,
Giang Vo-Thanh*
a   Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud, 91405 Orsay Cedex, France   eMail: giang.vo-thanh@u-psud.fr
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Publikationsverlauf

Received: 29. August 2013

Accepted after revision: 16. Oktober 2013

Publikationsdatum:
14. November 2013 (online)


Abstract

A short and flexible procedure for the preparation of seven chiral azolinium and five functionalized chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline has been developed. Moderate to good overall yields were obtained. Some NHC dimers and thiones were isolated. X-ray crystal structure determinations of two [Rh-NHC] complexes were also reported.

Supporting Information

 
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