Facile formation of β-hydroxyboronate esters by a Cu-catalyzed diboration/Matteson homologation sequence.

ABSTRACT: 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.

SUBMITTER: Moore CM 

PROVIDER: S-EPMC4260635 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature