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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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 (50–99%, 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.).

Original language	English
Pages (from-to)	3502-3506
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	14
DOIs	https://doi.org/10.1002/adsc.202100408
Publication status	Published - 2021 Jul 20

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202100408

Cite this

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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 (50–99%, 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.).",

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",

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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

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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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 2057233: Experimental Crystal Structure Determination

CCDC 2057219: Experimental Crystal Structure Determination

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

Abstract

Keywords

ASJC Scopus subject areas

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Other files and links

Fingerprint

Datasets

CCDC 2057233: Experimental Crystal Structure Determination

CCDC 2057219: Experimental Crystal Structure Determination

Cite this