1357173-68-2Relevant academic research and scientific papers
Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes
Brazeau, Jean-Francois,Zhang, Suyan,Colomer, Ignacio,Corkey, Britton K.,Toste, F. Dean
supporting information; experimental part, p. 2742 - 2749 (2012/03/22)
The discovery of complementary methods for enantioselective transition metal-catalyzed cyclization with silyloxyenynes has been accomplished using chiral phosphine ligands. Under palladium catalysis, 1,6-silyloxyenynes bearing a terminal alkyne led to the desired five-membered ring with high enantioselectivities (up to 91% ee). As for reactions under cationic gold catalysis, 1,6-and 1,5-silyloxyenynes bearing an internal alkyne furnished the chiral cyclopentane derivatives with excellent enantiomeric excess (up to 94% ee). Modification of the substrate by incorporating an α,β- unsaturation led to the discovery of a tandem cyclization. Remarkably, using silyloxy-1,3-dien-7-ynes under gold catalysis conditions provided the bicyclic derivatives with excellent diastereo-and enantioselectivities (up to >20:1 dr and 99% ee).
