Enantioselective Synthesis of Both Axially and Planar Chiral Ferrocenes via Axial-to-Planar Diastereoinduction

Ferrocenes with planar chirality have emerged as an important class of scaffolds for ligands in asymmetric catalysis; however, ferrocene molecules with polychiral structures have not been well explored. Herein, both axially and planar chiral ferrocenes were synthesized via palladium/chiral norbornen...

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Published inOrganic letters Vol. 24; no. 40; pp. 7294 - 7299
Main Authors An, Yang, Zhang, Xiao-Yan, Ding, Ya-Nan, Li, Yuke, Liu, Xue-Yuan, Liang, Yong-Min
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.10.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
LIGANDS
ANNULATION
KINETIC RESOLUTION
PHOSPHINES
REDOX
DERIVATIVES
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Summary:Ferrocenes with planar chirality have emerged as an important class of scaffolds for ligands in asymmetric catalysis; however, ferrocene molecules with polychiral structures have not been well explored. Herein, both axially and planar chiral ferrocenes were synthesized via palladium/chiral norbornene cooperative catalysis and axial-to-planar diastereoinduction. In this work, chiral norbornene was used to stereoselectively control the aromatic axial chirality, and further selectivity induced C­(sp2)–H activation for ferrocene planar chirality. Based on density functional theory calculations, the catalytic model of chiral norbornene with the substrate and the axial-to-planar diastereoinduction process were confirmed.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02707