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Silver(I) Oxide‐/DBU‐Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation
Author(s) -
Yu Bao,
Perfetto Anna,
Allievi Luca,
Dhambri Sabrina,
Rager MarieNoelle,
Selkti Mohamed,
Ciofini Ilaria,
Lannou MarieIsabelle,
Sorin Geoffroy
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002696
Subject(s) - yield (engineering) , silver oxide , chemistry , oxide , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
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.