Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols.

ABSTRACT: The regioselective gold-catalysed hydration of propargylic alcohols to ?-hydroxy ketones can be achieved by diverting the gold-catalysed Meyer-Schuster rearrangement through the addition of a protic additive with a pKa of 7-9 such as p-nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an alkyne to an aldehyde or ketone. The gold-catalysed reaction of an electron-deficient, sterically hindered propargylic alcohol with a boronic acid led to the formation of an unusually stable cyclic boron enolate.

SUBMITTER: Pennell MN 

PROVIDER: S-EPMC5698882 | biostudies-other | 2016 Apr

REPOSITORIES: biostudies-other