Copper-Catalyzed Diboration of Ketones: Facile Synthesis of Tertiary α-Hydroxyboronate Esters

Melissa L. McIntosh, Cameron M. Moore and Timothy B. Clark*

*Department of Chemistry, Western Washington University, 516 High Street, Bellingham, Washington 98225, Email: clarkchem.wwu.edu

M. L. McIntosh, C. M. Moore, T. B. Clark, Org. Lett., 2010, 12, 1996-1999.

DOI: 10.1021/ol100468f

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Abstract

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.

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Key Words

boronates, α-hydroxyboronates

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ID: J54-Y2010-1240