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

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

Authors :
Yu B
Perfetto A
Allievi L
Dhambri S
Rager MN
Selkti M
Ciofini I
Lannou MI
Sorin G
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Dec 23; Vol. 26 (72), pp. 17455-17461. Date of Electronic Publication: 2020 Dec 01.
Publication Year :
2020

Abstract

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.<br /> (© 2020 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3765
Volume :
26
Issue :
72
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
32978998
Full Text :
https://doi.org/10.1002/chem.202002696