Enantioselective Synthesis of Planar Chiral Ferrocene Triflones

Abstract A multi‐gram scale synthesis of ferrocenetriflone was optimised from ferrocenesulfonyl fluoride and Me 3 SiCF 3 (Ruppert reagent). Enantioselective deprotolithiations were then optimised using alkyllithiums in the presence of catalytic (+)‐sparteine to afford 2‐substituted ferrocene triflones in 79–84% ee . The use of chiral lithium amides in the presence of in situ traps was also optimised and was found to outperform alkyllithium⋅chiral diamine chelates for the first time in the ferrocene series, with 89–93% ee . Crystallisation of derivatives afforded enantiopure compounds that were engaged in deprotolithiation‐electrophilic trapping sequences, a halogen ‘dance’ reaction and transition metal‐promoted coupling to afford a wide range of variously polysubstituted ferrocene triflones.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-09-04
DOI
https://doi.org/10.1002/adsc.202400834
Citations
2
Primary Topic
Coordination Chemistry and Organometallics
Type
article
Field-Weighted Citation Impact
0.50

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article

Enantioselective Synthesis of Planar Chiral Ferrocene Triflones

Jean‐Pierre Hurvois, Yury S. Halauko, Y Kitazawa, William Erb et al.
2 citations
Advanced Synthesis & Catalysis
Coordination Chemistry and Organometallics
0.50
article

Enantioselective Synthesis of Planar Chiral Ferrocene Triflones

Jean‐Pierre Hurvois, Yury S. Halauko, Y Kitazawa, William Erb, Thierry Roisnel, Mutsumi Kimura, Florence Mongin, Marielle Blot, Masanobu Uchiyama, Min Wen, Вадим Э. Матулис, Yuta Koike
article en
2 citations

Abstract

Abstract A multi‐gram scale synthesis of ferrocenetriflone was optimised from ferrocenesulfonyl fluoride and Me 3 SiCF 3 (Ruppert reagent). Enantioselective deprotolithiations were then optimised using alkyllithiums in the presence of catalytic (+)‐sparteine to afford 2‐substituted ferrocene triflones in 79–84% ee . The use of chiral lithium amides in the presence of in situ traps was also optimised and was found to outperform alkyllithium⋅chiral diamine chelates for the first time in the ferrocene series, with 89–93% ee . Crystallisation of derivatives afforded enantiopure compounds that were engaged in deprotolithiation‐electrophilic trapping sequences, a halogen ‘dance’ reaction and transition metal‐promoted coupling to afford a wide range of variously polysubstituted ferrocene triflones.

Advanced Synthesis & CatalysisVol. 366(24)
Centre National de la Recherche Scientifique (FR), Shinshu University (JP), Belarusian State University (BY), Institut des Sciences Chimiques de Rennes (FR), STMicroelectronics (France) (FR), Shinshu University Hospital (JP), Université de Rennes (FR), The University of Tokyo (JP)
Agence Nationale de la Recherche, European Regional Development Fund
Openalex Percentile: Top 40%
Coordination Chemistry and Organometallics
0.50
DOIOpen Access PDFOpenAlex
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