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Hokkaido University Collection of Scholarly and Academic Papers >
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Asymmetric Synthesis of beta-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand
| Title: | Asymmetric Synthesis of beta-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand |
| Authors: | Takayama, Yurie Browse this author | | Ishii, Takaoki Browse this author | | Ohmiya, Hirohisa Browse this author →KAKEN DB | | Iwai, Tomohiro Browse this author →KAKEN DB | | Schwarzer, Martin C. Browse this author | | Mori, Seiji Browse this author | | Taniguchi, Tohru Browse this author →KAKEN DB | | Monde, Kenji Browse this author →KAKEN DB | | Sawamura, Masaya Browse this author →KAKEN DB |
| Keywords: | asymmetric catalysis | | cooperative catalysis | | copper | | nitrones | | beta-lactam |
| Issue Date: | 22-Jun-2017 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Chemistry-A European journal |
| Volume: | 23 |
| Issue: | 35 |
| Start Page: | 8400 |
| End Page: | 8404 |
| Publisher DOI: | 10.1002/chem.201702070 |
| PMID: | 28488338 |
| Abstract: | Prolinol-phosphine chiral ligands enabled highly enantioselective copper-catalyzed intermolecular alkyne-nitrone coupling (Kinugasa reaction) to produce 1,3,4-trisubstituted chiral beta-lactams. A high level of enantiocontrol was achieved not only with aryl-or alkenylacetylenes but also with alkylacetylenes, which were important but unfavorable substrates in the previously reported protocols. Two-point hydrogen bonding between the chiral ligand and the nitrone oxyanion consisting of O-H center dot center dot center dot O and C(sp(3)) H center dot center dot center dot O hydrogen bonds is proposed. |
| Rights: | This is the peer reviewed version of the following article: Y. Takayama, T. Ishii, H. Ohmiya, T. Iwai, M. C. Schwarzer, S. Mori, T. Taniguchi, K. Monde, M. Sawamura, Chem. Eur. J. 2017, 23, 8400, which has been published in final form at doi:10.1002/chem.201702070. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for Self-archiving. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/70659 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 澤村 正也
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