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Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
E-mail: yejx@ecust.edu.cn
Chem. Commun., 2012,48, 9180-9182
DOI:
10.1039/C2CC34321E
Received
16 Jun 2012,
Accepted
23 Jul 2012
First published online
06 Aug 2012
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.