22354-39-8Relevant articles and documents
Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
, p. 5054 - 5059 (2021/07/20)
An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
α,β-Unsaturated ketones via copper(II) bromide mediated oxidation
Sharley, James S.,Collado Pérez, Ana María,Ferri, Estela Espinos,Miranda, Amadeo Fernandez,Baxendale, Ian R.
supporting information, p. 2947 - 2954 (2016/05/19)
A protocol for effecting a rapid Saegusa-type oxidation of enol acetates is reported. This new method relies on the in situ elimination of an α-bromo intermediate to generate α,β-unsaturated ketones using copper(II) bromide. The methodology developed was applied to a range of substrates including a cyclohexanone, which could be directly converted to the corresponding phenol derivative. A catalytic system in which a non-masked ketone was successfully oxidised using substoichiometric CuBr2 was also developed as a proof of principle.
Copper/palladium-catalyzed 1,4 reduction and asymmetric allylic alkylation of α,β-unsaturated ketones: Enantioselective dual catalysis
Nahra, Fady,Mace, Yohan,Lambin, Dominique,Riant, Olivier
, p. 3208 - 3212 (2013/04/23)
Cooperative efforts: The catalytic coupling of the two organometallic intermediates is possible through a Cu/Pd-based dual catalysis (see scheme; LG=leaving group), in which the CuI catalytic cycle generates catalytically the starting material
