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タイトル: | Impact of Catalyst Deuteration on the Reactivity of Chiral Phase‐Transfer Organocatalysts |
著者: | Murayama, Sei Li, Zhurong Liang, Huatai Liu, Yan Naka, Hiroshi https://orcid.org/0000-0002-1198-6835 (unconfirmed) Maruoka, Keiji |
著者名の別形: | 村山, 聖 中, 寛史 丸岡, 啓二 |
キーワード: | asymmetric catalysis deuteration kinetic isotope effects organocatalysis phase-transfer catalysis |
発行日: | 21-Sep-2023 |
出版者: | Wiley |
誌名: | Chemistry – A European Journal |
巻: | 29 |
号: | 53 |
論文番号: | e202301866 |
抄録: | Site-specifically deuterated organocatalysts were prepared and found to show improved reactivity over the non-deuterated analogs. Two privileged C₂-symmetric chiral binaphthyl-modified tetraalkylammonium salts were selected for this study. The stability of these phase-transfer catalysts was generally improved by site-specific deuteration, though the degree of improvement was structure dependent. In particular, a large secondary kinetic isotope effect was observed for the tetradeuterated phase-transfer catalyst. The performance of these deuterated catalysts in the asymmetric catalytic alkylation of amino acid derivatives was better than that of non-deuterated analogs at low catalyst loadings. The results suggest that catalyst deuteration is a promising strategy for enhancing the stability and performance of organocatalysts. |
著作権等: | This is the peer reviewed version of the following article: [Murayama, S., Li, Z., Liang, H., Liu, Y., Naka, H., Maruoka, K., Chem. Eur. J. 2023, 29, e202301866.], which has been published in final form at https://doi.org/10.1002/chem.202301866. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. The full-text file will be made open to the public on 28 July 2024 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
URI: | http://hdl.handle.net/2433/285221 |
DOI(出版社版): | 10.1002/chem.202301866 |
PubMed ID: | 37332072 |
出現コレクション: | 学術雑誌掲載論文等 |
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