The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the α-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260635 | PMC |
| http://dx.doi.org/10.1021/ol502767m | DOI Listing |
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