Chemical Communications 2012-09-21

Asymmetric construction of spirocyclohexanonerhodanines catalyzed by simple diamine derived from chiral tert-leucine.

Wenbin Wu, Huicai Huang, Xiaoqian Yuan, Kailong Zhu, Jinxing Ye

Index: Chem. Commun. (Camb.) 48(73) , 9180-2, (2012)

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Abstract

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.