Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

You Song Cheng; Shih Hsien Chan; Gunda Ananda Rao; Ramani Gurubrahamam; Kwunmin Chen

doi:10.1002/adsc.202100408

Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

You Song Cheng
, Shih Hsien Chan
, Gunda Ananda Rao
, Ramani Gurubrahamam^*
, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

14 引文斯高帕斯（Scopus）

摘要

An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ⁴-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50–99%, 55–>99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).

原文	英語
頁（從 - 到）	3502-3506
頁數	5
期刊	Advanced Synthesis and Catalysis
卷	363
發行號	14
DOIs	https://doi.org/10.1002/adsc.202100408
出版狀態	已發佈 - 2021 7月 20

ASJC Scopus subject areas

催化
有機化學

存取文件

10.1002/adsc.202100408

其它文件與鏈接

CCDC 2057219: Experimental Crystal Structure Determination
Cheng, Y.-S. (Contributor), Chan, S.-H. (Contributor), Rao, G. A. (Contributor), Gurubrahamam, R. (Contributor) & Chen, K. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc271pxx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc271pxx&sid=DataCite
資料集: Dataset
CCDC 2057233: Experimental Crystal Structure Determination
Cheng, Y.-S. (Contributor), Chan, S.-H. (Contributor), Rao, G. A. (Contributor), Gurubrahamam, R. (Contributor) & Chen, K. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc271qcd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc271qcd&sid=DataCite
資料集: Dataset

引用此

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title = "Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis",

abstract = "An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ4-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50{\textendash}99\%, 55{\textendash}>99\% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).",

keywords = "2,3-dihydroisoxazole, aza-Friedel-Crafts reaction, chiral phosphoric acid, ion-pair catalysis, organocatalysis",

author = "Cheng, \{You Song\} and Chan, \{Shih Hsien\} and Rao, \{Gunda Ananda\} and Ramani Gurubrahamam and Kwunmin Chen",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = jul,

day = "20",

doi = "10.1002/adsc.202100408",

language = "English",

volume = "363",

pages = "3502--3506",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "14",

}

TY - JOUR

T1 - Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

AU - Cheng, You Song

AU - Chan, Shih Hsien

AU - Rao, Gunda Ananda

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2021/7/20

Y1 - 2021/7/20

N2 - An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ4-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50–99%, 55–>99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).

AB - An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ4-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50–99%, 55–>99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).

KW - 2,3-dihydroisoxazole

KW - aza-Friedel-Crafts reaction

KW - chiral phosphoric acid

KW - ion-pair catalysis

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85108885179

UR - https://www.scopus.com/pages/publications/85108885179#tab=citedBy

U2 - 10.1002/adsc.202100408

DO - 10.1002/adsc.202100408

M3 - Article

AN - SCOPUS:85108885179

SN - 1615-4150

VL - 363

SP - 3502

EP - 3506

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14

ER -

Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2057219: Experimental Crystal Structure Determination

CCDC 2057233: Experimental Crystal Structure Determination

引用此