Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions

Xiaokang Lv; Jun Xu; Cuiyun Sun; Fen Su; Yuanlin Cai; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acscatal.2c00001

Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions

Xiaokang Lv, Jun Xu, Cuiyun Sun, Fen Su, Yuanlin Cai, Zhichao Jin^*, Yonggui Robin Chi^*

^*Corresponding author for this work

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

42 Citations (Scopus)

Abstract

Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development.

Original language	English
Pages (from-to)	2706-2713
Number of pages	8
Journal	ACS Catalysis
Volume	12
Issue number	4
DOIs	https://doi.org/10.1021/acscatal.2c00001
Publication status	Published - Feb 18 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 American Chemical Society

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

antibacterial activity
ferrocene derivatives
N-heterocyclic carbene
organocatalysis
planar chiral molecule synthesis

Access to Document

10.1021/acscatal.2c00001

Cite this

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abstract = "Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development.",

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author = "Xiaokang Lv and Jun Xu and Cuiyun Sun and Fen Su and Yuanlin Cai and Zhichao Jin and Chi, {Yonggui Robin}",

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T1 - Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions

AU - Lv, Xiaokang

AU - Xu, Jun

AU - Sun, Cuiyun

AU - Su, Fen

AU - Cai, Yuanlin

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2022/2/18

Y1 - 2022/2/18

N2 - Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development.

AB - Ferrocene-derived dicarbaldehydes bearing pro-chiral planes are desymmetrized under the catalysis of chiral N-heterocyclic carbene organic catalysts. The reaction features selective activation and reaction of one of the aldehyde moieties of the ferrocene derivative while leaving the other aldehyde unit untouched. Our reaction affords enantiomerically enriched planar chiral ferrocene products obtained that are amenable for further transformations. Preliminary application studies show encouraging results when our products are explored for catalysis in chemical synthesis and for antimicrobial utilities in pesticide development.

KW - antibacterial activity

KW - ferrocene derivatives

KW - N-heterocyclic carbene

KW - organocatalysis

KW - planar chiral molecule synthesis

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DO - 10.1021/acscatal.2c00001

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Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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