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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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/20/4811 |
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doaj-1213928bd06a4c509bda197243a83cf32020-11-25T03:56:48ZengMDPI AGMolecules1420-30492020-10-01254811481110.3390/molecules25204811Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical StudyMarc Presset0Michel Rajzmann1Guillaume Dauvergne2Jean Rodriguez3Yoann Coquerel4Aix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, FranceAix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, FranceAix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, FranceAix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, FranceAix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, FranceInversions 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.https://www.mdpi.com/1420-3049/25/20/4811hetero-Diels–Alderketenesiminesperiselectivitydensity functional theory |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Marc Presset Michel Rajzmann Guillaume Dauvergne Jean Rodriguez Yoann Coquerel |
| spellingShingle |
Marc Presset Michel Rajzmann Guillaume Dauvergne Jean Rodriguez Yoann Coquerel Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study Molecules hetero-Diels–Alder ketenes imines periselectivity density functional theory |
| author_facet |
Marc Presset Michel Rajzmann Guillaume Dauvergne Jean Rodriguez Yoann Coquerel |
| author_sort |
Marc Presset |
| title |
Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study |
| title_short |
Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study |
| title_full |
Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study |
| title_fullStr |
Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study |
| title_full_unstemmed |
Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study |
| title_sort |
periselectivity in the aza-diels–alder reaction of 1-azadienes with α-oxoketenes: a combined experimental and theoretical study |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2020-10-01 |
| description |
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. |
| topic |
hetero-Diels–Alder ketenes imines periselectivity density functional theory |
| url |
https://www.mdpi.com/1420-3049/25/20/4811 |
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