1236384-35-2Relevant academic research and scientific papers
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.
Asymmetric synthesis of 3, 4-diaminochroman-2-ones promoted by guanidine and bisguanidium salt
Dong, Shunxi,Liu, Xiaohua,Zhang, Yulong,Lin, Lili,Feng, Xiaoming
supporting information; experimental part, p. 5060 - 5063 (2011/12/05)
A highly enantioselective synthesis of 3,4-diaminochroman-2-ones has been realized via the domino reaction of o-hydroxy aromatic aldimines and azlactones. Notably, a cis-product was obtained as the major product by the use of guanidine 2a whereas a trans-product was the major product with bisguanidium salt 3·HBArF 4. In two cases, various substituted 3,4-dihydrocoumarins were obtained with high yields (up to 99%) as well as excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >99:1 cis:trans and 98:2 trans:cis, respectively) under mild reaction conditions.
