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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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Publication details

The article was received on 30 Oct 2014, accepted on 26 Nov 2014 and first published on 26 Nov 2014


Article type: Communication
DOI: 10.1039/C4CC08598A
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Citation: Chem. Commun., 2015,51, 5246-5249

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    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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