5453-88-3Relevant articles and documents
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Dubois,J.-E.,Fort,J.-F.
, p. 1653 - 1663 (1972)
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Facile synthesis of δ-ketoesters via formal two-carbon insertion into β-ketoesters
Jiang, Yan,Xi, Song,Wang, Qi,Fu, Lin,He, Ling,Wang, Zhen,Zhang, Min
supporting information, (2022/02/10)
A formal two-carbon insertion into β-ketoesters with vinylmetal has been developed for the rapid synthesis of δ-ketoesters. This method features high efficiency, simple operation, and mild conditions without the usage of bases and catalysts. The reaction is postulated to proceed via a tandem process involving nucleophilic addition of vinylmetal to ketone, retro-aldol reaction to give an enolate anion and an enone, and finally Michael addition of these two intermediates.
Oxidative umpolung ?±-alkylation of ketones
Shneider, O. Svetlana,Pisarevsky, Evgeni,Fristrup, Peter,Szpilman, Alex M.
supporting information, p. 282 - 285 (2015/03/05)
We disclose a hypervalent iodine mediated ?±-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The ?±-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.
Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran e and Other Targets of Interest
Blaisdell, Thomas P.,Morken, James P.
supporting information, p. 8712 - 8715 (2015/07/27)
A hydroxyl functional group positioned β to a pinacol boronate can serve to direct palladium-catalyzed cross-coupling reactions. This feature can be used to control the reaction site in multiply borylated substrates and can activate boronates for reaction that would otherwise be unreactive.