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

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

Chemical communications (Cambridge, England) (2012-08-07)
Wenbin Wu, Huicai Huang, Xiaoqian Yuan, Kailong Zhu, Jinxing Ye
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Rhodanine, 97%
Sigma-Aldrich
L-tert-Leucine, 99%