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Synthesis of α-hydroxyboronates

Recent Literature

In a catalytic enantioselective nucleophilic borylation, a series of aldehydes reacted with B₂pin₂ in the presence of a copper(I)/DTBM-SEGPHOS complex as catalyst and MeOH as a proton source to give the corresponding optically active α-alkoxyorganoboronate esters with excellent enantioselectivities. These products can readily be converted to chiral alcohol derivatives through stereospecific C-C bond forming reactions.
K. Kubota, E. Yamamoto, H. Ito, J. Am. Chem. Soc., 2015, 137, 420-424.

Visible-light-induced B-H insertions of HBpin with acylsilane proceed in an atom-economical, metal-free, and operationally simple way with broad substrate scope under mild reaction conditions, to provide important α-alkoxyorganoboronate esters in quantitative yields.
J.-H. Ye, L. Quach, T. Paulisch, F. Glorius, J. Am. Chem. Soc., 2019, 141, 16227-16231.

Diboration of ketones with (ICy)CuOt-Bu as catalyst provides access to various tertiary α-hydroxyboronate esters. The catalyst was generated in situ with (ICy)CuCl and NaOt-Bu to afford a more efficient catalyst than the preformed (ICy)CuOt-Bu. Treatment of the resulting products with silica gel affords the corresponding α-hydroxyboronate esters.
M. L. McIntosh, C. M. Moore, T. B. Clark, Org. Lett., 2010, 12, 1996-1999.

A ruthenium-catalyzed hydroboration of ynones provides vinyl α-hydroxylboronates under mild conditions. This reaction features high efficiency, a broad scope, and complete chemo-, regio-, and stereoselectivity, in spite of many possible competitive pathways.
Q. Feng, S. Li, Z. Li, Q. Yan, X. Lin, L. Song, X. Zhang, Y.-D. Wu, J. Sun, J. Am. Chem. Soc., 2022, 144, 14846-14855.