Asymmetric tandem reactions based on nitroalkenes:: a one-pot construction of functionalized chiral bicycles by a three-component reaction

被引:16
作者
Avalos, M [1 ]
Babiano, R [1 ]
Cintas, P [1 ]
Jiménez, JL [1 ]
Palacios, JC [1 ]
Silva, MA [1 ]
机构
[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain
关键词
D O I
10.1039/a708222c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric tandem cycloaddition of a chiral carbohydrate nitroalkene with ethyl vinyl ether in the presence of electron-withdrawing alkenes produces a facile assembly of bicyclic systems, which can further be selectively cleaved to give homologated carbohydrates.
引用
收藏
页码:459 / 460
页数:2
相关论文
共 17 条
[1]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[2]   Substrate-controlled stereodifferentiation of tandem [4+2]/[3+2] cycloadditions by a vicinal carbohydrate-based template [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Higes, FJ ;
Jimenez, JL ;
Palacios, JC ;
Silva, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1880-1882
[3]   RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].
BUNCE, RA .
TETRAHEDRON, 1995, 51 (48) :13103-13159
[4]  
BUTLER RN, 1992, J CHEM RES, P256
[5]  
CARRUTHERS W, 1990, CYCLOADDITION REACTI, P293
[6]   Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].
Denmark, SE ;
Thorarensen, A .
CHEMICAL REVIEWS, 1996, 96 (01) :137-165
[7]   STEREOSELECTIVE HOMOLOGATION - AMINATION OF ALDEHYDES BY ADDITION OF THEIR NITRONES TO C-2 METALATED THIAZOLES - A GENERAL ENTRY TO ALPHA-AMINO ALDEHYDES AND AMINO-SUGARS [J].
DONDONI, A ;
FRANCO, S ;
JUNQUERA, F ;
MERCHAN, FL ;
MERINO, P ;
TEJERO, T ;
BERTOLASI, V .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (08) :505-520
[8]   Stereoselective addition of 2-furyllithium and 2-thiazolyllithium to sugar nitrones. Synthesis of carbon-linked glycoglycines [J].
Dondoni, A ;
Junquera, F ;
Merchan, FL ;
Merino, P ;
Scherrmann, MC ;
Tejero, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5484-5496
[9]   Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].
Frederickson, M .
TETRAHEDRON, 1997, 53 (02) :403-425
[10]  
Ho T.-L., 1992, TANDEM ORGANIC REACT