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 journalArticle

17 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 languageEnglish
Pages (from-to)5246-5249
Number of pages4
JournalChemical Communications
Volume51
Issue number25
DOIs
Publication statusPublished - 2015 Mar 28
Externally publishedYes

Fingerprint

Enantioselectivity
Aldehydes
Esters
Alcohols
Derivatives
Acids
allyl alcohol

ASJC Scopus subject areas

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

Cite this

γ-Silylboronates in the chiral Brønsted acid-catalysed allylboration of aldehydes. / Barrio, Pablo; Rodríguez, Elsa; Saito, Kodai; Fustero, Santos; Akiyama, Takahiko.

In: Chemical Communications, Vol. 51, No. 25, 28.03.2015, p. 5246-5249.

Research output: Contribution to journalArticle

Barrio, Pablo ; Rodríguez, Elsa ; Saito, Kodai ; Fustero, Santos ; Akiyama, Takahiko. / γ-Silylboronates in the chiral Brønsted acid-catalysed allylboration of aldehydes. In: Chemical Communications. 2015 ; Vol. 51, No. 25. pp. 5246-5249.
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