Borylation and rearrangement of alkynyloxiranes: a stereospecific route to substituted α-enynes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2019

Borylation and rearrangement of alkynyloxiranes: a stereospecific route to substituted α-enynes

Ruben Pomar Fuentespina
  • Fonction : Auteur
José Angel Garcia de La Cruz
  • Fonction : Auteur
Gabriel Durin
  • Fonction : Auteur
Victor Mamane
Patrick Pale

Résumé

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes. 1416
Fichier principal
Vignette du fichier
BJOC2019.pdf (607.64 Ko) Télécharger le fichier
Origine : Publication financée par une institution
Loading...

Dates et versions

hal-02266110 , version 1 (15-05-2020)

Identifiants

Citer

Ruben Pomar Fuentespina, José Angel Garcia de La Cruz, Gabriel Durin, Victor Mamane, Jean-Marc Weibel, et al.. Borylation and rearrangement of alkynyloxiranes: a stereospecific route to substituted α-enynes. Beilstein Journal of Organic Chemistry, 2019, 15, pp.1416-1424. ⟨10.3762/bjoc.15.141⟩. ⟨hal-02266110⟩
37 Consultations
50 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More