66421-85-0Relevant academic research and scientific papers
Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation
Nimmagadda, Sri Krishna,Liu, Mingyu,Karunananda, Malkanthi K.,Gao, De-Wei,Apolinar, Omar,Chen, Jason S.,Liu, Peng,Engle, Keary M.
, p. 3923 - 3927 (2019/03/07)
A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with nonconjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction, and a cleavable bidentate directing group appended to the alkene to control the regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal reaction conditions to afford products bearing α,α-disubstituted α-amino-acid derivatives with high yields and high enantioselectivity.
Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction
Hu, Haipeng,Liu, Yangbin,Guo, Jing,Lin, Lili,Xu, Yali,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 3835 - 3837 (2015/03/31)
An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N′-dioxide-Sc(iii) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19:1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.
Organocatalytic oxyamination of azlactones: Kinetic resolution of oxaziridines and asymmetric synthesis of oxazolin-4-ones
Dong, Shunxi,Liu, Xiaohua,Zhu, Yin,He, Peng,Lin, Lili,Feng, Xiaoming
supporting information, p. 10026 - 10029 (2013/07/26)
The first example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and successfully used in the asymmetric oxyamination of 3-methyl-1H-indole and styrene. The triple stereodifferentiation process was also studied via control experiments.
A versatile and stereoselective synthesis of fnnctionalized cyclobutenes
Frebault, Frederic,Luparia, Marco,Oliveira, Maria Teresa,Goddard, Richard,Maulide, Nuno
supporting information; experimental part, p. 5672 - 5676 (2010/10/21)
(Figure Presented) Square flat: A new atom-economical method for the synthesis of functionalized cyclobutenes has been developed. This versatile sequence hinges upon a unique combination of an elegant photochemical isomerization and a palladium-catalyzed
Synthesis and biological activity of some new 1,3,4-thiadiazole and 1,2,4-triazole compounds containing a phenylalanine moiety
Moise, Mihaela,Sunel, Valeriu,Profire, Lenuta,Popa, Marcel,Desbrieres, Jacques,Peptu, Cristian
experimental part, p. 2621 - 2631 (2009/12/06)
New 1,3,4-thiadiazole, 6, 7 and 1,2,4-triazole derivatives, 8, 9 containing a phenylalanine moiety have been synthesized by intramolecular cyclization of 1,4- disubstituted thiosemicarbazides, 4, 5, in acid and alkaline media, respectively; the thiosemica
