The copper-catalyzed diboration of
aldehydes was used in conjunction
with the Matteson homologation, providing the efficient synthesis
of β-hydroxyboronate esters. The oxygen-bound boronate ester
was found to play a key role in mediating the homologation reaction,
which was compared to the α-hydroxyboronate ester (isolated
hydrolysis product). The synthetic utility of the diboration/homologation
sequence was demonstrated through the oxidation of one product to
provide a 1,2-diol.
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