Exploiting the σ-phylic properties of cationic gold(i) catalysts in the ring opening reactions of aziridines with indoles. Issue 25 (2nd June 2016)

• Record Type: Journal Article
• Authors: Rossi, Elisabetta; Abbiati, Giorgio; Dell'Acqua, Monica; Negrato, Marco; Paganoni, Andrea; Pirovano, Valentina
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 25(2016)
• Page Start: 6095
• Page End: 6110
• Publication Date: 2016-06-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00672h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Gold(i ) species catalyze the ring opening reactions of aziridines with indoles as nucleophiles for the synthesis of tryptamines and pyrroloindolines. Abstract : A study on the SN 2-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.