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Org Lett. 2018 Sep 7;20(17):5112-5115. doi: 10.1021/acs.orglett.8b01948. Epub 2018 Aug 24.

Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids.

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1
Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Republic of Singapore 117543.

Abstract

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In particular, the use of enantiopure aziridines delivers disubstituted tetrahydropyrimidines bearing a 1,3-diamino unit in good yields as a single stereoisomer (>20:1 dr, > 99% ee). The heterocyclic products can also be easily converted to synthetically useful amino alcohol derivatives or α,γ-diamino acids.

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