title: 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.
authors.affiliation: Dipartimento di Scienze Farmaceutiche - Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, Via G. Venezian, 21 - 20133 Milano, Italy. elisabetta.rossi@unimi.it.
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Rossi
authors.forename: Giorgio
authors.initials: G
authors.lastname: Abbiati
authors.forename: Monica
authors.initials: M
authors.lastname: Dell'Acqua
authors.forename: Marco
authors.initials: M
authors.lastname: Negrato
authors.forename: Andrea
authors.initials: A
authors.lastname: Paganoni
authors.forename: Valentina
authors.initials: V
authors.lastname: Pirovano