Asymmetric 1,3-dipolar cycloaddition reaction of azomethine imines to allyl alcohol

被引:37
作者
Kato, Tomomitsu [1 ]
Fujinami, Shuhei [1 ]
Ukaji, Yutaka [1 ]
Inomata, Katsuhiko [1 ]
机构
[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Dept Mat Sci, Kanazawa, Ishikawa 9201192, Japan
关键词
D O I
10.1246/cl.2008.342
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric 1,3-dipolar cycloaddition of azomethine imines to allyl alcohol was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active trans-pyrazolidines with excellent regio-, diastereo-, and enantioselectivities.
引用
收藏
页码:342 / 343
页数:2
相关论文
共 26 条
[1]   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
[2]   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
[3]  
DIAZOALKANES S, 2000, J AM CHEM SOC, V122, P10710
[4]  
Gothelf KV, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P211
[5]   Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2000, (16) :1449-1458
[6]  
Kanemasa S, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P249
[7]   Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and α-substituted acroleins:: Total synthesis of manzacidin A [J].
Kano, T ;
Hashimoto, T ;
Maruoka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2174-2175
[8]   Asymmetric intramolecular [3+2] cycloaddition reactions of acylhydrazones/olefins using a chiral zirconium catalyst [J].
Kobayashi, S ;
Shimizu, H ;
Yamashita, Y ;
Ishitani, H ;
Kobayashi, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13678-13679
[9]   Catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol utilizing diisopropyl tartrate as a chiral auxiliary [J].
Shimizu, M ;
Ukaji, Y ;
Inomata, K .
CHEMISTRY LETTERS, 1996, (06) :455-456
[10]   A new copper-catalyzed [3+2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles [J].
Shintani, R ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10778-10779