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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
Published on: July 23, 2016
Enantioselective alkenylation and phenylation catalyzed by a chiral CuF complex
Daisuke Tomita1, Reiko Wada, Motomu Kanai
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Abstract:
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. The key to success partly involves the accelerated regeneration of reactive alkenylcopper and phenylcopper through transmetalation from the silylated nucleophiles, and stabilization of the reactive copper reagents, both of which are effected by the diphosphine ligands.
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