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Asymmetric Synthesis of beta-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand

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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)

Submitter: 澤村 正也

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