Silver(I) Oxide-/DBU-Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation.

Bao YuAnna Perfetto Luca AllieviSabrina DhambriMarie-Noelle RagerMohamed Selkti Ilaria Ciofini Marie-Isabelle Lannou Geoffroy Sorin

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)

A formal [3+2] cyclization mediated by silver(I) oxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is described herein. Through a broad variety of carbonyl compounds, this system can promote cyclization reactions with high yield (up to 85 %) and diastereoselectivity (up to 95:5) for a straightforward access to complex and congested dihydrofuran derivatives in one step under mild conditions. Based on DFT studies, the proposed mechanism would involve an allenyl silver intermediate.

Keyphrases

gold nanoparticles
silver nanoparticles
molecular docking
density functional theory
molecular dynamics simulations