The transmetalation between RuCl2(PPh3)((R,R)-Me-bipam)
and ArBFn(OH)(3ꢀn) generated by the reaction of ArB(OH)2
and KF may provide the arylruthenium(II) intermediate
RuCl(Ar)(PPh3)((R,R)-Me-bipam), which is analogous to a Ph–Cl
exchange between PhB(OH)2 and [RuCl2(p-cymene)(PPh3)].17
Although isolation of the intermediate RuCl(Ph)(PPh3)((R,R)-
Me-bipam) failed, the reaction of phenylboronic acid and
RuCl2(p-cymene)(PPh3)18 in the presence of KF gave RuCl(Ph)-
(p-cymene)(PPh3) in 61% yield (eqn (2)).17b,19 The enantio-
selectivity is determined at insertion of the C–O double bond into
the C–Ru bond of RuCl(Ar)(PPh3)((R,R)-Me-bipam) complex.
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ð2Þ
In conclusion, we have developed a RuCl2(PPh3)3/(R,R)-
Me-BIPAM catalyst as an efficient catalytic system for asymmetric
addition of arylboronic acids to glyoxylate. With this catalyst
system, optically active mandelic acids were easily prepared in up
to 99% ee. To elucidate the enantioselection in the mechanism,
characterization of the catalyst and the intermediate is in progress.
This work was supported in part by the Global COE Program
(Project No. B01, Catalysis as the Basis for Innovation in
Materials Science) from the Ministry of Education, Culture,
Sports, Science and Technology, Japan.
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This journal is The Royal Society of Chemistry 2012
Chem. Commun., 2012, 48, 2803–2805 2805