Song Y,
Zou Y,
Chen T,
Zhang Z *,
Zhang W *.
Shanghai Jiao Tong University, P. R. China
Cobalt-Catalyzed Asymmetric Hydrogenation of α-Hydroxy Ketones Enabled by a Carboxylic
Acid Additive Promotion Strategy.
Angew. Chem. Int. Ed. 2025;
64: e202504159
DOI:
10.1002/anie.202504159
Keywords
α-hydroxy ketones - asymmetric hydrogenation - chiral 1,2-diols - cobalt catalysis
Significance
A carboxylic acid additive was found to significantly increase the reactivity and
enantioselectivity of a cobalt(II)-catalyzed asymmetric hydrogenation of α-hydroxy
ketones. This protocol provides facile access to highly enantioenriched 1,2-diols,
which are important building blocks in synthetic chemistry.
Comment
When the α-hydroxy group is replaced by an ester or a methoxy group, the yield of
the reaction is
markedly reduced. This suggests that the proton of the hydroxy group plays a key
role in the catalytic activity of this transformation. This result along with
further DFT studies support the shown catalytic cycle.
