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Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

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Title: Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers
Authors: Zhou, Hui Browse this author
Han, Jung Tae Browse this author
Noethling, Nils Browse this author
Lindner, Monika M. Browse this author
Jenniches, Judith Browse this author
Kuehn, Clemens Browse this author
Tsuji, Nobuya Browse this author →KAKEN DB
Zhang, Li Browse this author
List, Benjamin Browse this author →KAKEN DB
Keywords: Aromatic compounds
Catalysts
Group 14 compounds
Hydrocarbons
Inorganic compounds
Issue Date: 1-Jun-2022
Publisher: American Chemical Society
Journal Title: Journal of the American Chemical Society
Volume: 144
Issue: 23
Start Page: 10156
End Page: 10161
Publisher DOI: 10.1021/jacs.2c04261
Abstract: Functionalized enantiopure organosilanes are important building blocks with applications in various fields of chemistry; nevertheless, asymmetric synthetic methods for their preparation are rare. Here we report the first organocatalytic enantioselective synthesis of tertiary silyl ethers possessing central chirality on silicon. The reaction proceeds via a desymmetrizing carbon-carbon bond forming silicon-hydrogen exchange reaction of symmetrical bis(methallyl)silanes with phenols using newly developed imidodiphosphoriinidate (IDPi) catalysts. A variety of enantiopure silyl ethers was obtained in high yields with good chemo- and enantioselectivities and could be readily derivatized to several useful chiral silicon compounds, leveraging the olefin functionality and the leaving group nature of the phenoxy substituent.
Type: article
URI: http://hdl.handle.net/2115/86370
Appears in Collections:化学反応創成研究拠点:ICReDD (Institute for Chemical Reaction Design and Discovery : ICReDD) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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