Rearrangement Processes of Oxonium and Ammonium Ylides Formed by Rhodium(II)-Catalyzed Carbene Transfer

ChemInform ◽  
2005 ◽  
Vol 36 (33) ◽  
Author(s):  
Frederick F. West
Keyword(s):  
Carbene Transfer ◽  
Rearrangement Processes

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

scholarly journals Homoleptic and heteroleptic bis-NHC Cu(i) complexes as carbene transfer reagents

2016 ◽  
Vol 45 (12) ◽  
pp. 4970-4973 ◽  
Author(s):  
Orlando Santoro ◽  
Faïma Lazreg ◽  
David B. Cordes ◽  
Alexandra M. Z. Slawin ◽  
Catherine S. J. Cazin
Keyword(s):  
Carbene Transfer

Homo- and heteroleptic bis-NHC copper(i) complexes have been efficiently used as carbene transfer reagents to Au and Pd.

Review of gold(I) N-heterocyclic carbenes

2005 ◽  
Vol 83 (6-7) ◽  
pp. 812-825 ◽  
Author(s):  
Ivan JB Lin ◽  
Chandra Sekhar Vasam
Keyword(s):  
Liquid Crystal ◽  
Heterocyclic Carbenes ◽  
Supramolecular Assemblies ◽  
Easy Method ◽  
Carbene Transfer

This review presents an overview of the work on Au(I)–NHC chemistry. The efficiency of different synthetic strategies of Au(I)–NHCs is discussed. Transmetallation of Ag(I)–NHCs appears to be an easy method as compared with the others. The influence of aurophilicity "a traditional property of a Au(I) center" in making the supramolecular assemblies is also covered. The combination of the Au(I) center with NHCs has great potential in the fields of medicine, catalysis, liquid crystal, and optoelectronic.Key words: gold–carbenes, silver–carbenes, carbene transfer, aurophilicity.

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