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Issue 25, 2015
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γ-Silylboronates in the chiral Brønsted acid-catalysed allylboration of aldehydes

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Abstract

The use of functionalised allylboronic esters in the catalytic enantioselective allylboration of aldehydes is described for the first time. γ-Silylallyl pinacolate derivatives give rise to α-silyl homoallylic alcohols in high yields, with complete diastereoselectivities and high enantioselectivities, in most of the cases. The usefulness of such intermediates is showcased by their transformation into fluorinated allylic alcohols.

Graphical abstract: γ-Silylboronates in the chiral Brønsted acid-catalysed allylboration of aldehydes

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Article information


Submitted
30 Oct 2014
Accepted
26 Nov 2014
First published
26 Nov 2014

Chem. Commun., 2015,51, 5246-5249
Article type
Communication
Author version available

γ-Silylboronates in the chiral Brønsted acid-catalysed allylboration of aldehydes

P. Barrio, E. Rodríguez, K. Saito, S. Fustero and T. Akiyama, Chem. Commun., 2015, 51, 5246
DOI: 10.1039/C4CC08598A

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