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Enantioselective Direct Alkynylation of Ketones Catalyzed by Chiral CCN Pincer Rh III Complexes
Author(s) -
Ito Junichi,
Ubukata Shino,
Muraoka Shun,
Nishiyama Hisao
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603754
Subject(s) - alkynylation , catalysis , chemistry , propargyl , enantioselective synthesis , oxazoline , pincer movement , carbene , medicinal chemistry , organic chemistry
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, ArCOCF 2 X (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.
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