Organocatalytic DYKAT of Si-Stereogenic Silanes

Zhou, Hui; Properzi, Roberta; Leutzsch, Markus et al.

Journal of the American Chemical Society, 2023, 145(9), 4994-5000

Permalink : https://hdl.handle.net/2115/89038

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https://doi.org/10.1021/jacs.3c00858     35

論文情報

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アクセス権
open access
URI
https://hdl.handle.net/2115/89038
タイトル
Organocatalytic DYKAT of Si-Stereogenic Silanes
著者
Zhou, Hui ; Properzi, Roberta ; Leutzsch, Markus ; Belanzoni, Paola ; Bistoni, Giovanni ; Tsuji, Nobuya ; Han, Jung Tae ; Zhu, Chendan ; List, Benjamin
著者名
Zhou, Hui
著者名
Properzi, Roberta
著者名
Leutzsch, Markus
著者名
Belanzoni, Paola
著者名
Bistoni, Giovanni
e-Rad_Researcher
30873575
著者名
Tsuji, Nobuya
著者名
Han, Jung Tae
著者名
Zhu, Chendan
e-Rad_Researcher
80899253
著者名
List, Benjamin
言語
英語
発行日
2023-02-24
出版者
American Chemical Society
収録物名
Journal of the American Chemical Society
巻(号)
145(9)
ページ
4994-5000
抄録
Chiral organosilanes do not exist in nature and are therefore absent from the chiral pool. As a consequence, synthetic approaches toward enantiopure silanes, stereogenic at silicon, are rather limited. While catalytic asymmetric desymmetrization reactions of symmetric organosilicon compounds have been developed, the utilization of racemic silanes in a dynamic kinetic asymmetric transformation (DYKAT) or dynamic kinetic resolution (DKR) would significantly expand the breadth of accessible Si-stereogenic compounds. We now report a DYKAT of racemic allyl silanes enabled by strong and confined imidodiphosphorimidate (IDPi) catalysts, providing access to Si-stereogenic silyl ethers. The products of this reaction are easily converted into useful enantiopure monohydrosilanes. We propose a spectroscopically and experimentally supported mechanism involving the epimerization of a catalyst-bound intermediate.
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.3c00858