Synfacts 2020; 16(02): 0209
DOI: 10.1055/s-0039-1691613
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organoselenium-Catalyzed Asymmetric syn-Diamination of Alkenes

Benjamin List
Yihang Li
Tao Z, Gilbert BB, Denmark SE. * University of Illinois, Urbana, USA
Catalytic, Enantioselective syn-Diamination of Alkenes.

J. Am. Chem. Soc. 2019;
141: 19161-19170
Further Information

Publication History

Publication Date:
21 January 2020 (online)



Denmark and co-workers report an intermolecular enantioselective diamination of alkenes by using a chiral arylselenium reagent as a redox catalyst. A wide variety of trans-1,2-disubstituted imidazolidin-2-ones were obtained in yields of up to 89% and with er values of up to 98:2.



By this method, aryl–alkyl or diaryl olefins were diaminated in good yields and with moderate to high enantioselectivities. However, poor reactivity was observed with dialkyl substrates, which limits the general applicability of this reaction.