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

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19 Scopus citations

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.
Original languageEnglish (US)
JournalOrganic Chemistry Frontiers
DOIs
StatePublished - Jun 23 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-07-15
Acknowledgements: This work was supported by JSPS KAKENHI Grant Numbers 20K15281 for Early-Career Scientists, JP17H05373 and JP18KK0154 in Promotion of Joint International Research (Fostering Joint International Research(B)), JST CREST Grant Number JPMJCR20R1, Daiichi Sankyo Foundation of Life, Hoansha Foundation, Iwatani Naoji foundation, and the NOVARTIS Foundation (Japan) for the Promotion of Science. We acknowledge the technical staff of the Comprehensive Analysis Center of ISIR, and Artificial Intelligence Research Center of ISIR, Osaka University (Japan).

ASJC Scopus subject areas

  • Organic Chemistry

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