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. 2019 May 17;21(10):3760-3763.
doi: 10.1021/acs.orglett.9b01204. Epub 2019 May 8.

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

Lu Yan  1 , James P Morken  1
Affiliations

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

Lu Yan et al. Org Lett. .

Abstract

Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

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Figures

Scheme 1.
Scheme 1.
Site-Selective Functionalization of 1,2-Bis(boronates).
Scheme 2.
Scheme 2.
Prospective Selectivity Paradigms in Vicinal Diboronate Oxidation Reactions.
See this image and copyright information in PMC

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