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, 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 language	English (US)
Journal	Organic Chemistry Frontiers
DOIs	https://doi.org/10.1039/d1qo00783a
State	Published - Jun 23 2021

ASJC Scopus subject areas

Organic Chemistry

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10.1039/d1qo00783a

https://repository.kaust.edu.sa/bitstream/10754/670186/1/Manuscript%20%289%29.pdf

Cite this

@article{7f1366596b70484d9acebb1b91d111d0,

title = "Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex",

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.",

author = "Makoto Sako and Keigo Higashida and Kamble, {Ganesh Tatya} and Kevin Kaut and Ankit Kumar and Yuka Hirose and Da-Yang Zhou and Takeyuki Suzuki and Magnus Rueping and Tomohiro Maegawa and Shinobu Takizawa and Hiroaki Sasai",

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).",

year = "2021",

month = jun,

day = "23",

doi = "10.1039/d1qo00783a",

language = "English (US)",

journal = "Organic Chemistry Frontiers",

issn = "2052-4129",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex

AU - Sako, Makoto

AU - Higashida, Keigo

AU - Kamble, Ganesh Tatya

AU - Kaut, Kevin

AU - Kumar, Ankit

AU - Hirose, Yuka

AU - Zhou, Da-Yang

AU - Suzuki, Takeyuki

AU - Rueping, Magnus

AU - Maegawa, Tomohiro

AU - Takizawa, Shinobu

AU - Sasai, Hiroaki

N1 - 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).

PY - 2021/6/23

Y1 - 2021/6/23

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/670186

UR - http://xlink.rsc.org/?DOI=D1QO00783A

U2 - 10.1039/d1qo00783a

DO - 10.1039/d1qo00783a

M3 - Article

SN - 2052-4129

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

ER -

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

Abstract

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CCDC 1966275: Experimental Crystal Structure Determination : 11-(2-hydroxynaphthalen-1-yl)-7H-benzo[c]carbazol-10-ol ethyl acetate solvate

CCDC 2025416: Experimental Crystal Structure Determination : methyl 10-bromo-3a-hydroxy-1,2,3,3a-tetrahydrocyclopenta[4,5]furo[2,3-c]carbazole-11d(7H)-carboxylate ethyl acetate solvate

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1966275: Experimental Crystal Structure Determination : 11-(2-hydroxynaphthalen-1-yl)-7H-benzo[c]carbazol-10-ol ethyl acetate solvate

CCDC 2025416: Experimental Crystal Structure Determination : methyl 10-bromo-3a-hydroxy-1,2,3,3a-tetrahydrocyclopenta[4,5]furo[2,3-c]carbazole-11d(7H)-carboxylate ethyl acetate solvate

Cite this