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Site-Selective Mono-Oxidation of 1,2-Bis(boronates)

Lu Yan, James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu

L. Yan, J. P. Morken, Org. Lett., 2019, 21, 3760-3763.

DOI: 10.1021/acs.orglett.9b01204 (free Supporting Information)



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Abstract

The use of N-oxides in butanol as solvent enables a site-selective oxidation of vicinal bis(boronates) with good efficiency and selectivity across a range of substrates to provide 2-hydro-1-boronic esters, which are shown to be versatile intermediates in the synthesis of chiral building blocks.

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Key Words

boration, hydroxylation, NMO, organocatalysis


ID: J54-Y2019