29373-01-1Relevant articles and documents
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones
Trongsiriwat, Nisalak,Li, Minyan,Pascual-Escudero, Ana,Yucel, Baris,Walsh, Patrick J.
supporting information, p. 502 - 509 (2018/12/11)
Palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with in-situ generated 2-sodio-1,3-dithiane nucleophiles to afford the allylated products in good to excellent yields (25 examples). Deprotection of these products leads to valuable β,γ-unsaturated ketones. Direct synthesis of such β,γ-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Investigation into the stereochemistry of the allylation reaction revealed that the 2-sodio-1,3-dithiane nucleophile behaves as a “soft” nucleophile, which underwent external attack on the π-allyl palladium complex to provide retention of stereochemistry (double inversion pathway). Additionally, the utility of this method was demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives, which are important bioactive compounds in medicinal chemistry. (Figure presented.).
Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes
Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 106 - 109 (2017/11/27)
A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.
