Synthesis of Axially Chiral CF3-Substituted 2-Arylpyrroles by Sequential Phosphine-Catalyzed Asymmetric [3+2] Annulation and Oxidative Central-to-Axial Chirality Transfer

Chuan Xiang Alvin Tan; Rui Li; Fuhao Zhang; Lei Dai; Nisar Ullah; Yixin Lu

doi:10.1002/anie.202209494

Synthesis of Axially Chiral CF₃-Substituted 2-Arylpyrroles by Sequential Phosphine-Catalyzed Asymmetric [3+2] Annulation and Oxidative Central-to-Axial Chirality Transfer

Chuan Xiang Alvin Tan, Rui Li, Fuhao Zhang, Lei Dai, Nisar Ullah^*, Yixin Lu^*

^*Corresponding author for this work

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

21 Scopus citations

Abstract

A sequential phosphine-catalyzed asymmetric [3+2] annulation of aldimines with allenoates and oxidative central-to-axial chirality transfer strategy has been developed. This approach is operationally simple, allowing for rapid access to a range of axially chiral CF₃-containing 2-arylpyrroles with high enantiomeric excess. Furthermore, an atroposelective synthesis of esaxerenone is presented, illustrating the practical potential of the reported method.

Original language	English
Article number	e202209494
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	47
DOIs	https://doi.org/10.1002/anie.202209494
State	Published - 21 Nov 2022

Bibliographical note

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

Atroposelectivity
Axial Chirality
Chirality Transfer
Phosphine Catalysis
[3+2] Annulation

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.202209494

Cite this

@article{5fb3c71734514ad3a083569149667479,

title = "Synthesis of Axially Chiral CF3-Substituted 2-Arylpyrroles by Sequential Phosphine-Catalyzed Asymmetric [3+2] Annulation and Oxidative Central-to-Axial Chirality Transfer",

abstract = "A sequential phosphine-catalyzed asymmetric [3+2] annulation of aldimines with allenoates and oxidative central-to-axial chirality transfer strategy has been developed. This approach is operationally simple, allowing for rapid access to a range of axially chiral CF3-containing 2-arylpyrroles with high enantiomeric excess. Furthermore, an atroposelective synthesis of esaxerenone is presented, illustrating the practical potential of the reported method.",

keywords = "Atroposelectivity, Axial Chirality, Chirality Transfer, Phosphine Catalysis, [3+2] Annulation",

author = "{Xiang Alvin Tan}, Chuan and Rui Li and Fuhao Zhang and Lei Dai and Nisar Ullah and Yixin Lu",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

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month = nov,

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doi = "10.1002/anie.202209494",

language = "English",

volume = "61",

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}

Synthesis of Axially Chiral CF₃-Substituted 2-Arylpyrroles by Sequential Phosphine-Catalyzed Asymmetric [3+2] Annulation and Oxidative Central-to-Axial Chirality Transfer. / Xiang Alvin Tan, Chuan; Li, Rui; Zhang, Fuhao et al.
In: Angewandte Chemie - International Edition, Vol. 61, No. 47, e202209494, 21.11.2022.

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

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AU - Xiang Alvin Tan, Chuan

AU - Li, Rui

AU - Zhang, Fuhao

AU - Dai, Lei

AU - Ullah, Nisar

AU - Lu, Yixin

PY - 2022/11/21

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AB - A sequential phosphine-catalyzed asymmetric [3+2] annulation of aldimines with allenoates and oxidative central-to-axial chirality transfer strategy has been developed. This approach is operationally simple, allowing for rapid access to a range of axially chiral CF3-containing 2-arylpyrroles with high enantiomeric excess. Furthermore, an atroposelective synthesis of esaxerenone is presented, illustrating the practical potential of the reported method.

KW - Atroposelectivity

KW - Axial Chirality

KW - Chirality Transfer

KW - Phosphine Catalysis

KW - [3+2] Annulation

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