Affiliation:
1. Institut für Organische und Biomolekulare Chemie Georg‐August‐Universität Göttingen Tammannstr 2 37077 Göttingen Germany
Abstract
AbstractA series of helically shaped benzo[b]chryseno[4,3‐d]thiophenes, naphtho[1,2‐b]phenanthro[4,3‐d]thiophenes, and chryseno[3,4‐b]naphtho[1,2‐d]thiophenes is synthesized via a highly enantioselective Au‐catalyzed intramolecular alkyne hydroarylation reaction. The inversion barriers of the structures obtained are determined both theoretically and experimentally, and their chiroptical properties are reported. Preliminary studies on the post‐synthetic functionalization of these thiahelicenes and their transformation into azahelicenes are also presented. In addition, a straightforward one‐step protocol is developed, which wraps the initially obtained chryseno[3,4‐b]naphtho[1,2‐d]thiophenes into bowl‐shaped pleiadene derivatives without erosion of the enantiopurity. The number of structurally related products that are obtained with high enantioselectivity enables the establishment of comprehensive correlations between the structure and conformational stability or (chir)optical properties.
Funder
Deutsche Forschungsgemeinschaft
China Scholarship Council
Subject
Mechanical Engineering,Mechanics of Materials,General Materials Science
Cited by
5 articles.
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