Issue 25, 2016

Exploiting the σ-phylic properties of cationic gold(i) catalysts in the ring opening reactions of aziridines with indoles

Abstract

A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(I) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(I) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in terms of catalyst loading and reaction yields. Moreover, complete regioselectivity was observed for 2-phenyl-N-tosylaziridine; whereas, regioselectivity up to 10 : 1 ratio was observed with 2-methyl-N-tosylaziridine. Finally, a preliminary study on the dearomatization reactions giving rise to pyrroloindolines is also reported.

Graphical abstract: Exploiting the σ-phylic properties of cationic gold(i) catalysts in the ring opening reactions of aziridines with indoles

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2016
Accepted
24 May 2016
First published
25 May 2016
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2016,14, 6095-6110

Author version available

Exploiting the σ-phylic properties of cationic gold(I) catalysts in the ring opening reactions of aziridines with indoles

E. Rossi, G. Abbiati, M. Dell'Acqua, M. Negrato, A. Paganoni and V. Pirovano, Org. Biomol. Chem., 2016, 14, 6095 DOI: 10.1039/C6OB00672H

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