Catalytic functionalization of low reactive C(sp3)–H and C(sp2)–H bonds of alkanes and arenes by carbene transfer from diazo compounds

2015 ◽  
Vol 44 (47) ◽  
pp. 20295-20307 ◽  
Author(s):  
Ana Caballero ◽  
M. Mar Díaz-Requejo ◽  
Manuel R. Fructos ◽  
Andrea Olmos ◽  
Juan Urbano ◽  
...  
ChemCatChem ◽  
2014 ◽  
Vol 6 (7) ◽  
pp. 2047-2052 ◽  
Author(s):  
Manuela Delgado-Rebollo ◽  
Auxiliadora Prieto ◽  
Pedro J. Pérez

ChemInform ◽  
2014 ◽  
Vol 46 (3) ◽  
pp. no-no
Author(s):  
Manuela Delgado-Rebollo ◽  
Auxiliadora Prieto ◽  
Pedro J. Perez

2019 ◽  
Vol 10 (34) ◽  
pp. 7958-7963 ◽  
Author(s):  
Ban Wang ◽  
Isaac G. Howard ◽  
Jackson W. Pope ◽  
Eric D. Conte ◽  
Yongming Deng

The bis(imino)pyridine iron complex, for the first time, is developed as an effective metal carbene catalyst for carbene transfer reactions of donor–acceptor diazo compounds.


2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  

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>


Author(s):  
V. S. Lenenko ◽  
A. P. Borisov ◽  
V. D. Makhaev ◽  
E. I. Mysov ◽  
V. B. Shur ◽  
...  
Keyword(s):  

Sign in / Sign up

Export Citation Format

Share Document