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Enantioselective Synthesis of 1,2-Benzothiazine 1-Imines via Ru-II/Chiral Carboxylic Acid-Catalyzed C-H Alkylation/Cyclization
| Title: | Enantioselective Synthesis of 1,2-Benzothiazine 1-Imines via Ru-II/Chiral Carboxylic Acid-Catalyzed C-H Alkylation/Cyclization |
| Authors: | Huang, Long-Tao Browse this author | | Kitakawa, Yuta Browse this author | | Yamada, Kodai Browse this author | | Kamiyama, Futa Browse this author | | Kojima, Masahiro Browse this author →KAKEN DB | | Yoshino, Tatsuhiko Browse this author →KAKEN DB | | Matsunaga, Shigeki Browse this author →KAKEN DB |
| Keywords: | 1,2-Benzothiazine 1-Imine | | Asymmetric Catalysis | | C-H Activation | | Ruthenium | | Sulfondiimine |
| Issue Date: | 17-May-2023 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Angewandte chemie-international edition |
| Volume: | 62 |
| Issue: | 29 |
| Start Page: | e202305480 |
| Publisher DOI: | 10.1002/anie.202305480 |
| Abstract: | Sulfondiimines are diaza-analogues of sulfones with a chiral sulfur center. Compared to sulfones and sulfoximines, their synthesis and transformations have so far been studied to a lesser extent. Here, we report the enantioselective synthesis of 1,2-benzothiazine 1-imines, i.e., cyclic sulfondiimine derivatives from sulfondiimines and sulfoxonium ylides via C-H alkylation/cyclization reactions. The combination of [Ru(p-cymene)Cl-2](2) and a newly developed chiral spiro carboxylic acid is key to achieving high enantioselectivity. |
| Rights: | This is the peer reviewed version of the following article: https://onlinelibrary.wiley.com/doi/10.1002/anie.202305480, which has been published in final form at 10.1002/anie.202305480. 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. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/92582 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉野 達彦
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