A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5, 6-tetrahydroimidazo[1,5-b]isoxazoles

被引:20
作者
Lu, Lei [1 ]
Cao, Weiguo [1 ,2 ,3 ]
Chen, Jie [1 ]
Zhang, Hui [1 ]
Zhang, Jiaping [1 ]
Chen, Huiyun [1 ]
Wei, Jiamei [1 ]
Deng, Hongmei [4 ]
Shao, Min [4 ]
机构
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[4] Shanghai Univ, Instrumental Anal & Res Ctr, Shanghai 200444, Peoples R China
基金
中国国家自然科学基金;
关键词
Methyl; 2-perfluoroalkynoates; Imidazoisoxazoles; 1,3-Dipolar cycloaddition; Diastereoselectivity; Regioselectivity; 1,3-DIPOLAR CYCLOADDITION REACTIONS; HETEROCYCLIC-COMPOUNDS; CYCLIC NITRONES; ISOXAZOLIDINES; ALKYNES; ROUTE; BOND;
D O I
10.1016/j.jfluchem.2008.11.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:295 / 300
页数:6
相关论文
共 51 条
[1]  
Banks R. E., 1994, ORGANOFLUORINE CHEM
[2]   ENHANCEMENT OF ALKENE REACTIVITY BY A TRIFLUOROMETHYL GROUP - SYNTHESIS OF PYRROLIDINES VIA 1,3-DIPOLAR CYCLOADDITION [J].
BEGUE, JP ;
BONNETDELPON, D ;
LEQUEUX, T .
TETRAHEDRON LETTERS, 1993, 34 (20) :3279-3282
[3]  
Burgart YV, 2006, HETEROCYCLES, V69, P593
[4]   FLUORO HETEROCYCLES WITH 5-MEMBERED RINGS [J].
BURGER, K ;
WUCHERPFENNIG, U ;
BRUNNER, E .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 60, 1994, 60 :1-64
[5]   Synthesis of partially fluorinated heterocycles from 4,4-bis(trifluoromethyl) substituted hetero-1,3-dienes via C-F bond activation and their application as trifluoromethyl substituted building blocks [J].
Burger, Klaus ;
Hennig, Lothar ;
Spengler, Jan ;
Albericio, Fernando .
HETEROCYCLES, 2006, 69 (01) :569-+
[6]  
*CAMBR CRYST DAT C, 651153 CCDC
[7]  
Chiacchio U, 1997, TARG HETEROCYCL SYST, V1, P225
[8]   Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles [J].
Coats, SJ ;
Link, JS ;
Gauthier, D ;
Hlasta, DJ .
ORGANIC LETTERS, 2005, 7 (08) :1469-1472
[9]   Synthesis of 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylic acid esters [J].
Coskun, N ;
Yilmaz, B .
SYNTHETIC COMMUNICATIONS, 2004, 34 (09) :1617-1623
[10]   Synthesis of di- and cis-triaryl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles and their ring-opening reactions [J].
Coskun, N ;
Tat, FT ;
Güven, ÖÖ .
TETRAHEDRON, 2001, 57 (16) :3413-3417