Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(V) complex

Makoto Sako; Keigo Higashida; Ganesh Tatya Kamble; Kevin Kaut; Ankit Kumar; Yuka Hirose; Da-Yang Zhou; Takeyuki Suzuki; Magnus Rueping; Tomohiro Maegawa; Shinobu Takizawa; Hiroaki Sasai

doi:10.1039/D1QO00783A

Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex†

Makoto Sako,

^a Keigo Higashida,^a Ganesh Tatya Kamble,^a Kevin Kaut,^ab Ankit Kumar,^a Yuka Hirose,^ac Da-Yang Zhou,^a Takeyuki Suzuki,

^a Magnus Rueping,

^bd Tomohiro Maegawa,

^c Shinobu Takizawa

*^a and Hiroaki Sasai

*^a

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* Corresponding authors

^a SANKEN (The Institute of Scientific and Industrial Research), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan
E-mail: taki@sanken.osaka-u.ac.jp, sasai@sanken.osaka-u.ac.jp

^b Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

^c School of Pharmaceutical Sciences, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan

^d Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia

Abstract

The catalytic enantioselective oxidative hetero-coupling of arenols using a chiral vanadium(V) complex has been developed. The coupling of hydroxycarbazole derivatives with various arenols provided axially chiral biarenols with high chemo-, regio-, and enantioselectivities. The reaction took place under mild conditions and exhibited satisfactory functional group tolerance. Aerobic oxidative hetero-coupling with β-ketoesters also proceeded with high chemo- and stereoselectivities under slightly modified reaction conditions.

Organic Chemistry Frontiers

Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex†

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Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(V) complex

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