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Monodentate non-C(2)-symmetric chiral N-heterocyclic carbene complexes for enantioselective synthesis. Cu-catalyzed conjugate additions of aryl- and alkenylsilylfluorides to cyclic enones.
J Org Chem
June 2009
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
A new class of enantioselective conjugate addition (ECA) reactions that involve aryl- or alkenylsilyl fluoride reagents and are catalyzed by chiral non-C(2)-symmetric Cu-based N-heterocyclic carbene (NHC) complexes are disclosed. Transformations have been designed based on the principle that a catalytically active chiral NHC-Cu-aryl or NHC-Cu-alkenyl complex can be accessed from reaction of a Cu-halide precursor with in situ-generated aryl- or alkenyltetrafluorosilicate. Reactions proceed in the presence of 1.
View Article and Find Full Text PDFHighly diastereoselective preparation of (E)-alkenylsilanes bearing an alpha-chiral center.
Org Lett
March 2007
Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, D-81377 München, Germany.
The copper(I)-mediated anti-S(N)2' allylic substitution allows a highly stereoselective preparation of alkenylsilanes bearing a chiral center in the alpha-position with high transfer of chirality. These alkenylsilanes were converted into alpha,beta-unsaturated ketones or into the corresponding boronic esters without loss of the chiral information. [reaction: see text]
View Article and Find Full Text PDFEnantioselective alkenylation and phenylation catalyzed by a chiral CuF complex.
J Am Chem Soc
March 2005
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
A new method for CuF-catalyzed alkenylation and phenylation of aldehydes and an activated ketone using air- and moisture-stable alkenylsilanes and phenylsilane as a nucleophile is described. This methodology was extended to highly enantioselective catalytic alkenylation and phenylation using DTBM-SEGPHOS as a chiral ligand. Substrate generality is broad, and an alkenylsilane with a long alkyl chain and an internal alkenylsilane can be also used as a nucleophile.
View Article and Find Full Text PDFFrom alkenylsilanes to ketones with air as the oxidant.
Angew Chem Int Ed Engl
February 2003
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
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