Abstract
The regioselective gold‐catalysed hydration of propargylic alcohols to β‐hydroxy ketones can be achieved by diverting the gold‐catalysed Meyer–Schuster rearrangement through the addition of a protic additive with a pK a 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.
Highlights
Propargylic alcohols are versatile compounds which can be used in a wide variety of gold-catalysed transformations.[1]
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
We describe our studies on the use of controlled protodemetallation to divert the gold-catalysed Meyer–Schuster rearrangement to give access to b-hydroxy ketones and related derivatives
Summary
Intercepting the gold-catalysed Meyer–Schuster rearrangement by controlled protodemetallation.
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