Kinetic Resolution of 2‐Substituted 1,2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation

Baohua Cai; Qingjing Yang; Ling Meng; Jun (Joelle) Wang

doi:10.1002/cjoc.202000742

Kinetic Resolution of 2‐Substituted 1,2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation

Baohua Cai
, Qingjing Yang
, Ling Meng
, Jun (Joelle) Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

14 Citations (Scopus)

Abstract

A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2-substituted 1,2-dihydroquinolines under mild reaction condition. The transformations into the enantio-enriched 2,3-diaryl-tetrahydroquinolines as well as the recovered chiral 2-aryl-dihydroquinolines were obtained with high yields and excellent enantioselectivities (86%—99% ee, s factor up to 1057).

Original language	English
Pages (from-to)	1606-1610
Number of pages	5
Journal	Chinese Journal of Chemistry
Volume	39
Issue number	6
Early online date	14 Feb 2021
DOIs	https://doi.org/10.1002/cjoc.202000742
Publication status	Published - Jun 2021

User-Defined Keywords

Asymmetric catalysis
Hydroarylation
Kinetic resolution
Tetrahydroquinoline
Transition metal

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10.1002/cjoc.202000742

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@article{63a64d50953243a797177385b6ba6c94,

title = "Kinetic Resolution of 2‐Substituted 1,2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation",

abstract = "A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2-substituted 1,2-dihydroquinolines under mild reaction condition. The transformations into the enantio-enriched 2,3-diaryl-tetrahydroquinolines as well as the recovered chiral 2-aryl-dihydroquinolines were obtained with high yields and excellent enantioselectivities (86\%—99\% ee, s factor up to 1057).",

keywords = "Asymmetric catalysis, Hydroarylation, Kinetic resolution, Tetrahydroquinoline, Transition metal",

author = "Baohua Cai and Qingjing Yang and Ling Meng and Wang, \{Jun (Joelle)\}",

note = "Funding Information: We gratefully acknowledge the Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (No. KQJSCX20180319114439973) for financial support. Funding Information: We gratefully acknowledge the Shenzhen Overseas High‐level Talents Innovation Plan of Technical Innovation Project (No. KQJSCX20180319114439973) for financial support. Publisher Copyright: {\textcopyright} 2021 SIOC, CAS, Shanghai and Wiley-VCH GmbH",

year = "2021",

month = jun,

doi = "10.1002/cjoc.202000742",

language = "English",

volume = "39",

pages = "1606--1610",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

publisher = "John Wiley \& Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Kinetic Resolution of 2‐Substituted 1,2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation

AU - Cai, Baohua

AU - Yang, Qingjing

AU - Meng, Ling

AU - Wang, Jun (Joelle)

N1 - Funding Information: We gratefully acknowledge the Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (No. KQJSCX20180319114439973) for financial support. Funding Information: We gratefully acknowledge the Shenzhen Overseas High‐level Talents Innovation Plan of Technical Innovation Project (No. KQJSCX20180319114439973) for financial support. Publisher Copyright: © 2021 SIOC, CAS, Shanghai and Wiley-VCH GmbH

PY - 2021/6

Y1 - 2021/6

N2 - A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2-substituted 1,2-dihydroquinolines under mild reaction condition. The transformations into the enantio-enriched 2,3-diaryl-tetrahydroquinolines as well as the recovered chiral 2-aryl-dihydroquinolines were obtained with high yields and excellent enantioselectivities (86%—99% ee, s factor up to 1057).

AB - A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via Rh-catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2-substituted 1,2-dihydroquinolines under mild reaction condition. The transformations into the enantio-enriched 2,3-diaryl-tetrahydroquinolines as well as the recovered chiral 2-aryl-dihydroquinolines were obtained with high yields and excellent enantioselectivities (86%—99% ee, s factor up to 1057).

KW - Asymmetric catalysis

KW - Hydroarylation

KW - Kinetic resolution

KW - Tetrahydroquinoline

KW - Transition metal

UR - https://www.scopus.com/pages/publications/85106298082

U2 - 10.1002/cjoc.202000742

DO - 10.1002/cjoc.202000742

M3 - Journal article

SN - 1001-604X

VL - 39

SP - 1606

EP - 1610

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 6

ER -

Kinetic Resolution of 2‐Substituted 1,2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation

Abstract

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