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Keywords = α-diazo lactams

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47 pages, 18460 KiB  
Review
Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds
by Daniil Zhukovsky, Dmitry Dar’in, Olga Bakulina and Mikhail Krasavin
Molecules 2022, 27(6), 2030; https://doi.org/10.3390/molecules27062030 - 21 Mar 2022
Cited by 7 | Viewed by 4787
Abstract
The reactivity of cyclic α-diazo monocarbonyl compounds differs from that of their acyclic counterparts. In this review, we summarize the current literature available on the synthesis and synthetic applications of three major classes of cyclic α-diazo monocarbonyl compounds: α-diazo ketones, α-diazo lactones and [...] Read more.
The reactivity of cyclic α-diazo monocarbonyl compounds differs from that of their acyclic counterparts. In this review, we summarize the current literature available on the synthesis and synthetic applications of three major classes of cyclic α-diazo monocarbonyl compounds: α-diazo ketones, α-diazo lactones and α-diazo lactams. Full article
(This article belongs to the Special Issue Chemistry of Nitrogen Heterocyclic Compounds)
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17 pages, 6350 KiB  
Article
Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of Catalysts and Substrate Substitution in the Synthesis of Oxindoles and β-Lactams
by Daniel Solé, Ferran Pérez-Janer, Arianna Amenta, M.-Lluïsa Bennasar and Israel Fernández
Molecules 2019, 24(19), 3551; https://doi.org/10.3390/molecules24193551 - 30 Sep 2019
Cited by 6 | Viewed by 3614
Abstract
The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation [...] Read more.
The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation states of Pd and a variety of ligands. It was found that, in the synthesis of oxindoles, ((IMes)Pd(NQ))2 can be used as an alternative to Pd2(dba)3 to catalyze the carbene CArsp2–H insertion, although it was less versatile. On the other hand, it was demonstrated that the Csp3–H insertion leading to β-lactams can be effectively promoted by both Pd(0) and Pd(II) catalysts, the latter being most efficient. Insight into the reaction mechanisms involved in these transformations was provided by DFT calculations. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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