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CrCl2-promoted stereospecific and stereoselective alkyl- and silylcyclopropanation of alpha,beta-unsaturated amides

Author:
Concellón Gracia, José ManuelUniovi authority; Rodríguez Solla, HumbertoUniovi authority; Méjica Iglesias, María del CarmenUniovi authority; Gutiérrez Blanco, ElenaUniovi authority; García-Granda, SantiagoUniovi authority; Díaz Fernández, María del RosarioUniovi authority
Publication date:
2008
Publisher version:
http://dx.doi.org/10.1021/jo800103t
Citación:
Journal of Organic Chemistry, v. 73(10), p. 3828-3836, (2008); doi:10.1021/jo800103t
Descripción física:
p. 3828-3836
Abstract:

An efficient chromium-promoted alkyl- or silylcyclopropanation of α,β-unsaturated amides is described. These reactions can be carried out on (E)- or (Z)-α,β-enamides in which the C−C double bond is di-, or trisubstituted. This process takes place with total stereospecificity and the new stereogenic center is generated with high or total stereoselectivity. Some synthetic applications of the obtained silylcyclopropyl amides are also reported. Two mechanisms based on the generation of carbenoid or carbene complexes have been proposed to explain this cyclopropanation reaction.

An efficient chromium-promoted alkyl- or silylcyclopropanation of α,β-unsaturated amides is described. These reactions can be carried out on (E)- or (Z)-α,β-enamides in which the C−C double bond is di-, or trisubstituted. This process takes place with total stereospecificity and the new stereogenic center is generated with high or total stereoselectivity. Some synthetic applications of the obtained silylcyclopropyl amides are also reported. Two mechanisms based on the generation of carbenoid or carbene complexes have been proposed to explain this cyclopropanation reaction.

URI:
http://hdl.handle.net/10651/7707
ISSN:
0022-3263
Identificador local:

729

DOI:
10.1021/jo800103t
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