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Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers
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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