Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study

Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study

Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some un...

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Bibliographic Details
Main Authors: Marc Presset, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel
Format: Article
Language:English
Published: MDPI AG 2020-10-01
Series:Molecules
Subjects:
hetero-Diels–Alder
ketenes
imines
periselectivity
density functional theory
Online Access:https://www.mdpi.com/1420-3049/25/20/4811
Description
Summary:Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.
ISSN:1420-3049

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