Issue 25, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
30 Nhl 2014
Accepted
26 Huk 2014
First published
26 Huk 2014

Chem. Commun., 2015,51, 5246-5249

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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