title: Chiral Triazoles in Anion-Binding Catalysis: New Entry to Enantioselective Reissert-Type Reactions.
abstract: Easily accessible and tunable chiral triazoles have been introduced as a novel class of C-H bond-based H-donors for anion-binding organocatalysis. They have proven to be effective catalysts for the dearomatization reaction of different N-heteroarenes. Although this dearomatization approach represents a powerful strategy to build chiral heterocycles, to date only a few catalytic methods to this end exist. In this work, the organocatalyzed enantioselective Reissert-type dearomatization of isoquinoline derivatives employing a number of structurally diverse chiral triazoles as anion-binding catalysts was realized. The here presented method was employed to synthesize a number of chiral 1,2-dihydroisoquinoline substrates with an enantioselectivity up to 86:14 e.r. Moreover, a thorough study of the determining parameters affecting the activity of this type of anion- binding catalysts was carried out.
authors.affiliation: Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.|Straubing Center of Science for Renewable Resources (WZS), Schulgasse 16, 94315, Straubing, Germany.
authors.forename: Mercedes
authors.initials: M
authors.lastname: Zurro
authors.affiliation: Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.
authors.forename: Sören
authors.initials: S
authors.lastname: Asmus
authors.affiliation: Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.
authors.forename: Julia
authors.initials: J
authors.lastname: Bamberger
authors.affiliation: Institute of Organic Chemistry, University of Münster, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Beckendorf
authors.affiliation: Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany. olga.garcia-mancheno@ur.de.|Straubing Center of Science for Renewable Resources (WZS), Schulgasse 16, 94315, Straubing, Germany. olga.garcia-mancheno@ur.de.
authors.forename: Olga
authors.identifier: http://orcid.org/0000-0002-7578-5418
authors.initials: O
authors.lastname: García Mancheño
keywords: anion-binding; enantioselective reactions; isoquinolines; organocatalysis; triazoles