Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

Zhou, Hui; Han, Jung Tae; Noethling, Nils; Lindner, Monika M.; Jenniches, Judith; Kuehn, Clemens; Tsuji, Nobuya; Zhang, Li; List, Benjamin

Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

Zhou, Hui; Han, Jung Tae; Noethling, Nils et al.

Journal of the American Chemical Society, 2022, 144(23), 10156-10161

Permalink : https://hdl.handle.net/2115/86370

このアイテムのアクセス数:538件（2026-03-20 11:17 集計）

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https://doi.org/10.1021/jacs.2c04261			2

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アクセス権	metadata only access
URI	https://hdl.handle.net/2115/86370
タイトル	Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers
著者	Zhou, Hui ; Han, Jung Tae ; Noethling, Nils ; Lindner, Monika M. ; Jenniches, Judith ; Kuehn, Clemens ; Tsuji, Nobuya ; Zhang, Li ; List, Benjamin
著者名 Zhou, Hui
著者名 Han, Jung Tae
著者名 Noethling, Nils
著者名 Lindner, Monika M.
著者名 Jenniches, Judith
著者名 Kuehn, Clemens
e-Rad_Researcher 30873575 著者名 Tsuji, Nobuya
著者名 Zhang, Li
e-Rad_Researcher 80899253 著者名 List, Benjamin
言語	英語
キーワード	Aromatic compounds
	Catalysts
	Group 14 compounds
	Hydrocarbons
	Inorganic compounds
発行日	2022-06-01
出版者	American Chemical Society
収録物名	Journal of the American Chemical Society
巻(号)	144(23)
ページ	10156-10161
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
PISSN	0002-7863
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.1021/jacs.2c04261