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Enantioselective Direct Alkynylation of Ketones Catalyzed by Chiral CCN Pincer RhIII Complexes
Authors:Dr Jun‐ichi Ito  Shino Ubukata  Shun Muraoka  Prof?Dr Hisao Nishiyama
Institution:Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Japan
Abstract:A direct asymmetric alkynylation of ketones with new chiral CCN Rh catalysts containing N‐heterocyclic carbene and oxazoline hybrid ligands is described. The catalytic reaction of fluoroalkyl‐substituted ketones, ArCOCF2X (X=F, Cl, H), with aromatic and aliphatic alkynes yielded the corresponding chiral propargyl alcohols with high enantioselectivity. Control and kinetic experiments suggested a bis(alkynyl) Rh intermediate as the active species for the C?C bond‐forming step.
Keywords:alkynylation  asymmetric synthesis  ketones  pincer ligands  rhodium
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