Development of a tailor-made bis(oxazolidine)pyridine-metal catalyst for the [3+2] cycloaddition of azomethine imines with propiolates

被引:56
作者
Arai, Takayoshi [1 ]
Ogino, Yuta [1 ]
Sato, Toru [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Chiba 2638522, Japan
关键词
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ALKYNYLATION; IMINOESTERS; COMPLEXES; LIGANDS; LIBRARY; EXO;
D O I
10.1039/c3cc44354j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of bis(oxazolidine)pyridine ligands (the PyBodines) were newly designed and synthesized for the development of a highly efficient, tailor-made catalyst for the [3+2] cycloaddition of azomethine imines with propiolates. The PyBodine(L-Ala)-Cu(OAc)(2) catalyst was selected on the basis of solid-phase catalysis/CD-HTS and exhibited high efficiency, producing the (R)-adducts with excellent enantioselectivity.
引用
收藏
页码:7776 / 7778
页数:3
相关论文
共 34 条
[1]   A library of chiral imidazoline-aminophenol ligands: Discovery of an efficient reaction sphere [J].
Arai, Takayoshi ;
Yokoyama, Naota ;
Yanagisawa, Akira .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) :2052-2059
[2]   Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism:: Diamine-CuI-catalyzed asymmetric Henry reaction [J].
Arai, Takayoshi ;
Watanabe, Masahiko ;
Fujiwara, Akitsugu ;
Yokoyama, Naota ;
Yanagisawa, Akira .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5978-5981
[3]   syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate Bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 Complex [J].
Arai, Takayoshi ;
Mishiro, Asami ;
Matsumura, Eri ;
Awata, Atsuko ;
Shirasugi, Mayu .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (36) :11219-11222
[4]   Chiral Bis(Imidazolidine) Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates [J].
Arai, Takayoshi ;
Ogino, Yuta .
MOLECULES, 2012, 17 (05) :6170-6178
[5]   Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition of Iminoesters with Nitroalkenes [J].
Arai, Takayoshi ;
Yokoyama, Naota ;
Mishiro, Asami ;
Sato, Hiroyasu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :7895-7898
[6]   Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes [J].
Arai, Takayoshi ;
Mishiro, Asami ;
Yokoyama, Naota ;
Suzuki, Kuniko ;
Sato, Hiroyasu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5338-+
[7]   Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation [J].
Bhor, S ;
Anilkumar, G ;
Tse, MK ;
Klawonn, M ;
Dobler, C ;
Bitterlich, B ;
Grotevendt, A ;
Beller, M .
ORGANIC LETTERS, 2005, 7 (16) :3393-3396
[8]   Developments in asymmetric catalysis by metal complexes of chiral chelating nitrogen-donor ligands [J].
Caputo, Christine A. ;
Jones, Nathan D. .
DALTON TRANSACTIONS, 2007, (41) :4627-4640
[9]   Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].
Chen, Wei ;
Du, Wei ;
Duan, Yong-Zheng ;
Wu, Yong ;
Yang, Sheng-Yong ;
Chen, Ying-Chun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670
[10]   Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].
Chen, Wei ;
Yuan, Xiang-Hong ;
Li, Rui ;
Du, Wei ;
Wu, Yong ;
Ding, Li-Sheng ;
Chen, Ying-Chun .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822