Literature DB >> 15592627

Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis.

Vincent César1, Stéphane Bellemin-Laponnaz, Lutz H Gade.   

Abstract

In recent years, N-heterocyclic carbenes (NHC) have proved to be a versatile class of spectator ligands in homogeneous catalysis. Being robust anchoring functions for late transition metals, their ligand donor capacity and their molecular shape is readily modified by variation of the substituents at the N-atoms and the structure of the cyclic backbone. After the first attempts to use chiral NHC ligands in asymmetric catalysis in the late 1990's, which initially met with limited success, several novel structural concepts have emerged during the past two years which have led literally to an explosion of the field. With a significant number of highly selective chiral catalysts based on chiral NHCs having been reported very recently, several general trends in the design of new NHC-containing molecular catalysts for stereoselective transformations in organic synthesis emerge.

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Year:  2004        PMID: 15592627     DOI: 10.1039/b406802p

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  39 in total

1.  CO fixation to stable acyclic and cyclic alkyl amino carbenes: stable amino ketenes with a small HOMO-LUMO gap.

Authors:  Vincent Lavallo; Yves Canac; Bruno Donnadieu; Wolfgang W Schoeller; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

2.  A rigid cyclic (alkyl)(amino)carbene ligand leads to isolation of low-coordinate transition-metal complexes.

Authors:  Vincent Lavallo; Yves Canac; Alan DeHope; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

3.  Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: a quaternary carbon atom makes the difference.

Authors:  Vincent Lavallo; Yves Canac; Carsten Präsang; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-05       Impact factor: 15.336

4.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

5.  Design and synthesis of C2-symmetric N-heterocyclic carbene precursors and metal carbenoids.

Authors:  Abigail Albright; Daniel Eddings; Regina Black; Christopher J Welch; Nikolay N Gerasimchuk; Robert E Gawley
Journal:  J Org Chem       Date:  2011-08-25       Impact factor: 4.354

6.  Synthesis and isolation of a stable, axially-chiral seven-membered N-heterocyclic carbene.

Authors:  Christopher C Scarborough; Ilia A Guzei; Shannon S Stahl
Journal:  Dalton Trans       Date:  2009-02-13       Impact factor: 4.390

7.  Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Authors:  Kyung Soo Yoo; Justin O'Neill; Satoshi Sakaguchi; Richard Giles; Joo Ho Lee; Kyung Woon Jung
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

8.  An unusual norcaradiene/tropylium rearrangement from a persistent amino-phosphonio-carbene.

Authors:  Joan Vignolle; Bruno Donnadieu; Didier Bourissou; Guy Bertrand
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

9.  A Facile Synthesis of Carbamoylsilanes, -boranes and -phosphane Oxides - Isolation of the First Uncomplexed Carbamoylborane.

Authors:  Yves Canac; Greg E Aniol; Salvador Conejero; Bruno Donnadieu; Guy Bertrand
Journal:  Eur J Inorg Chem       Date:  2006-12-01       Impact factor: 2.524

10.  Rearrangement of biaryl monoaminocarbenes via concerted asynchronous insertion into aromatic C-H bonds.

Authors:  Joan Vignolle; Matthew Asay; Karinne Miqueu; Didier Bourissou; Guy Bertrand
Journal:  Org Lett       Date:  2008-09-03       Impact factor: 6.005

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