Gold-Catalyzed Enantioselective Synthesis, Crystal Structure, and Photophysical/Chiroptical Properties of Aza[10]helicenes

Maya Tanaka; Yu Shibata; Kyosuke Nakamura; Kota Teraoka; Hidehiro Uekusa; Kazuko Nakazono; Toshikazu Takata; Ken Tanaka

doi:10.1002/chem.201601622

Gold-Catalyzed Enantioselective Synthesis, Crystal Structure, and Photophysical/Chiroptical Properties of Aza[10]helicenes

Chemistry. 2016 Jul 4;22(28):9537-41. doi: 10.1002/chem.201601622. Epub 2016 Jun 3.

Authors

Maya Tanaka^{1

2}, Yu Shibata¹, Kyosuke Nakamura², Kota Teraoka³, Hidehiro Uekusa³, Kazuko Nakazono⁴, Toshikazu Takata⁴, Ken Tanaka⁵

Affiliations

¹ Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
² Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
³ Department of Chemistry and Materials Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
⁴ Department of Organic and Polymeric Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan.
⁵ Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan. ktanaka@apc.titech.ac.jp.

PMID: 27128222
DOI: 10.1002/chem.201601622

Abstract

The enantioselective synthesis of an aza[10]helicene, possessing two pyridone units, has been achieved by the gold-catalyzed intramolecular quadruple hydroarylation of a tetrayne. This aza[10]helicene was successfully converted into a fully aromatic aza[10]helicene, possessing two pyridine units. Structure-photophysical and chiroptical properties relationship in a series of azahelicene isomers has also been disclosed.

Keywords: alkynes; asymmetric catalysis; azahelicenes; gold; hydroarylation.