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Article

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

Aix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France
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Authors to whom correspondence should be addressed.
Present address: Université Paris-Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, F-94320 Thiais, France.
Molecules 2020, 25(20), 4811; https://doi.org/10.3390/molecules25204811
Received: 25 September 2020 / Revised: 11 October 2020 / Accepted: 15 October 2020 / Published: 20 October 2020
(This article belongs to the Special Issue Diels-Alder Reaction in Organic Synthesis)
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. View Full-Text
Keywords: hetero-Diels–Alder; ketenes; imines; periselectivity; density functional theory hetero-Diels–Alder; ketenes; imines; periselectivity; density functional theory
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MDPI and ACS Style

Presset, M.; Rajzmann, M.; Dauvergne, G.; Rodriguez, J.; Coquerel, Y. Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study. Molecules 2020, 25, 4811. https://doi.org/10.3390/molecules25204811

AMA Style

Presset M, Rajzmann M, Dauvergne G, Rodriguez J, Coquerel Y. Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study. Molecules. 2020; 25(20):4811. https://doi.org/10.3390/molecules25204811

Chicago/Turabian Style

Presset, Marc, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, and Yoann Coquerel. 2020. "Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study" Molecules 25, no. 20: 4811. https://doi.org/10.3390/molecules25204811

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