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Organocatalytic DYKAT of Si-Stereogenic Silanes
| Title: | Organocatalytic DYKAT of Si-Stereogenic Silanes |
| Authors: | Zhou, Hui Browse this author | | Properzi, Roberta Browse this author | | Leutzsch, Markus Browse this author | | Belanzoni, Paola Browse this author | | Bistoni, Giovanni Browse this author | | Tsuji, Nobuya Browse this author →KAKEN DB | | Han, Jung Tae Browse this author | | Zhu, Chendan Browse this author | | List, Benjamin Browse this author →KAKEN DB |
| Issue Date: | 24-Feb-2023 |
| Publisher: | American Chemical Society |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 145 |
| Issue: | 9 |
| Start Page: | 4994 |
| End Page: | 5000 |
| Publisher DOI: | 10.1021/jacs.3c00858 |
| Abstract: | 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. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/89038 |
| 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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