Enantioselective Michael reaction of 2-nitropropane with substituted chalcones catalysed by chiral azacrown ethers derived from α-D-glucose

被引:63
作者
Bakó, T
Bakó, P
Szöllosy, A
Czugler, M
Keglevich, G
Toke, L
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Inst Gen & Analyt Chem, H-1521 Budapest, Hungary
[3] Hungarian Acad Sci, Chem Res Inst Chem, H-1525 Budapest, Hungary
[4] Budapest Univ Technol & Econ, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary
基金
匈牙利科学研究基金会;
关键词
D O I
10.1016/S0957-4166(02)00068-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The chiral monoaza-15-crown-5 lariat ethers anellated to methyl-4,6-O-benzylidene-alpha-D-glucopyranoside 1a-c showed significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to substituted chalcones. Among the catalysts bearing different side arms at the nitrogen atom, the compound with a phosphinoxidoalkyl side chain 1c proved to be the most effective (max. 78% e.e.). The type of substituent on the chalcone was found to have a very significant influence on both the chemical yield and the enantioselectivity of the reaction. The absolute configuration of the Michael adducts 3b and 3i was determined by chemical methods, while that of 3d was assigned by X-ray crystal structure determination. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:203 / 209
页数:7
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