1397692-16-8Relevant academic research and scientific papers
Enantioselective organocatalytic synthesis of sulfur-containing spirocyclic compounds
Geant, Pierre-Yves,Urban, Michal,Remes, Marek,Cisarova, Ivana,Vesely, Jan
, p. 7979 - 7988 (2014/01/06)
Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68 %) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99 % ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76 %) and with moderate-to-high selectivities (up to 12:1 dr, up to 90 % ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts. Benzothiophenone and N-phenylrhodanine were successfully used as bis-nucleophiles in two enantioselective organocatalytic cascades. Their reactions with enals and dienones allowed the formation of new sulfur-containing spirocyclic scaffolds in good yields and with high selectivities. Copyright
Asymmetric construction of spirocyclohexanonerhodanines catalyzed by simple diamine derived from chiral tert-leucine
Wu, Wenbin,Huang, Huicai,Yuan, Xiaoqian,Zhu, Kailong,Ye, Jinxing
supporting information; experimental part, p. 9180 - 9182 (2012/09/22)
A diamine-catalyzed asymmetric tandem reaction between α,β- unsaturated ketones and rhodanine derivatives has been developed to synthesize various spirocyclic compounds with high stereoselectivities (up to 99% ee and >20:1 dr). The products obtained contain two pharmaceutically relevant features: the biologically active rhodanine moiety embedded in a spirocyclic unit.
