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Enantioselective Direct Alkynylation of Ketones Catalyzed by Chiral CCN Pincer RhIII Complexes

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 ch...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-11, Vol.22 (47), p.16801-16804
Main Authors: Ito, Jun-ichi, Ubukata, Shino, Muraoka, Shun, Nishiyama, Hisao
Format: Article
Language:English
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Summary: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. A direct asymmetric alkynylation of ketones with new chiral CCN Rh catalysts containing N‐heterocyclic carbene and oxazoline hybrid ligands was 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201603754