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Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes

Matthew V. Joannou, Brandon S. Moyer and Simon J. Meek*

*Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: sjmeekunc.edu

M. V. Joannou, B. S. Moyer, S. J. Meek, J. Am. Chem. Soc., 2015, 137, 6176-6179.

DOI: 10.1021/jacs.5b03477 (free Supporting Information)


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Abstract

A catalytic enantio- and diastereoselective addition of alkyl 1,1-diboron reagents to aryl and vinyl aldehydes provides 1,2-hydroxyboronates promoted by a readily available chiral monodentate phosphoramidite-copper complex. Products contain two contiguous stereogenic centers and are obtained in good yield, good d.r., and high e.r. The 1,2-hydroxyboronate products can be transformed into versatile derivatives.

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Key Words

diols, sodium perborate


ID: J48-Y2015