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

Pablo Barrio; Elsa Rodríguez; Kodai Saito; Santos Fustero; Takahiko Akiyama

doi:10.1039/c4cc08598a

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

Pablo Barrio, Elsa Rodríguez, Kodai Saito, Santos Fustero, Takahiko Akiyama

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

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. This journal is

Original language	English
Pages (from-to)	5246-5249
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	25
DOIs	https://doi.org/10.1039/c4cc08598a
Publication status	Published - 2015 Mar 28
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c4cc08598a

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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. This journal is",

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AU - Barrio, Pablo

AU - Rodríguez, Elsa

AU - Saito, Kodai

AU - Fustero, Santos

AU - Akiyama, Takahiko

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2015/3/28

Y1 - 2015/3/28

N2 - 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. This journal is

AB - 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. This journal is

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JO - Chemical Communications

JF - Chemical Communications

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

Abstract

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