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Paper | Special issue | Vol 95, No. 1, 2017, pp.268-276
Published online, 18th October, 2016
DOI: 10.3987/COM-16-S(S)14
Synthesis of Unsymmetrical Heterobiaryls with Winding Vine-Shaped Molecular Asymmetry through a Condensation Pathway

Atsunori Mori,* Daichi Matsuoka, Shiomi Ashida, Ryo Inoue, Kazuki Maruhashi, Yoichi Okayama, Guan Hong Jin, and Kentaro Okano

*Chemical Science & Technology, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


Oxidative condensation of N-(3-buten-1-yl)-1,2-phenylenediamine with a formylated heteroarene bearing 3-buten-1-yl substituent gives unsymmetrical heterobiaryl in 42–86% yields. Ring-closing metathesis of the thus obtained product affords the cyclized product, which resulted in separation of each enantiomer by HPLC with a chiral column showing molecular asymmetry.