DFT studies on the mechanism of Pd(II)‐catalyzed intermolecular 1,2‐diamination of conjugated dienes

Yu, Youqing; Shen, Wei; Zhang, Jinsheng; He, Rongxing; Li, Ming

doi:10.1002/poc.1409

Cited by 5 publications

(1 citation statement)

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“…100 Finally, M. Li and co-workers have reported a DFT theoretical study on the palladium(II)-catalysed intermolecular 1,2-diamination of conjugated dienes. 101 1.5 Alkene aziridination 2008 has seen the publication of a review on the aziridination of a,b-unsaturated enones. 102 A significant development in this specific area was also communicated by Melchiorre and co-workers, who have described an organocatalytic asymmetric aziridination of a,b-unsaturated enones that has wide applicability and gives good stereoselectivity.…”

Section: Scheme 27mentioning

confidence: 99%

Synthetic methods : Part (ii) Oxidation and reduction methods

Lewis

2009

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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highlights advances in some of the most commonly used oxidation and reduction reactions, focusing on the literature from 2008. Significant advances in oxidation chemistry include site-selective epoxidation of polyprenols, 6 bis(hydroxamic acid) ligands for vanadium(V)-catalysed highly enantioselective epoxidation of cis-disubstituted olefins, 40 a direct catalytic aziridination of styrenes with ammonia 112 and an aerobic rutheniumcatalysed alkene to aldehyde oxidation displaying non-Wacker regiochemistry. 133 Significant advances in reduction chemistry include adaptive supramolecular ''METAMORPhos'' ligands for asymmetric alkene hydrogenation, 160 early main-group metal catalysts for alkene hydrogenation 181 and the use of ''frustrated Lewis pairs'' to effect H 2 bond scission for imine and nitrile reduction. 191 1 Oxidation reactions 1.1 Alkene epoxidation 2008 has seen the publication of reviews on aspects of epoxidation chemistry from Shi 1 (ketone and iminium organocatalysts), Linic 2 (heterogeneous catalysis), Katsuki 3 (Ti(salan) complexes) and Walsh 4 (tandem one-pot synthesis of epoxy alcohols). Oyama has also edited a book on epoxidation mechanisms. 5 Corey and Gnanadesikan have reported a strategy for the site-selective epoxidation of polyprenols that utilises silyl ether-linked aryl peracids to effect intramolecular epoxidation. 6 The method uses specific aryl motifs that may be varied to effect epoxidation of differing polyprenol double bonds (Scheme 1).The reactions are run at high dilution (0.5 mM) to minimise intermolecular oxygen transfer with respect to the desired intramolecular process. Corey and Gnanadesikan report achieving 92% selectivity for the D 14 olefin in a pentaprenol, or 89% selectivity for the D 18 olefin in a hexaprenol when employing a biaryl peracid.2008 has seen several advances in organocatalytic asymmetric alkene epoxidation. Deng and co-workers have reported a catalytic asymmetric epoxidation of a,b-unsaturated ketones, employing a cinchona alkaloid-derived catalyst for in situ iminium formation. 7 Significantly, reaction conditions have been optimised such that a simple change in reaction temperature is sufficient to alter the course of the reaction from epoxidation to peroxidation; in both instances up to 97% e.e. was achievable. (Scheme 2). The List group independently and simultaneously developed an extremely similar catalytic system.

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Section: Scheme 27mentioning

confidence: 99%