Asymmetric C-C bond forming reactions with chiral crown catalysts derived from D-glucose and D-galactose

被引:90
作者
Bakó, P
Czinege, E
Bakó, T
Czugler, M
Toke, L
机构
[1] Tech Univ Budapest, Dept Organ Chem Technol, Res Grp Hungarian Avad Sci, H-1521 Budapest, Hungary
[2] Hungarian Acad Sci, Cent Res Inst Chem, H-1525 Budapest, Hungary
基金
美国国家科学基金会; 匈牙利科学研究基金会;
关键词
D O I
10.1016/S0957-4166(99)00485-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New chiral monoaza-15-crown-5 derivatives anellated to methyl-4,6-O-benzylidene-alpha-D-glucopyranoside 2a, 2e, 2g-i and to methyl-4,6-O-benzylidene-alpha-D-galactopyranoside 3a, 3e, 3i have been synthesized. These crown ethers showed significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (87% ee), in the Darzens condensation of phenacyl chloride with benzaldehyde (71% ee) and in the self-condensation of phenacyl chloride (64% ee) to give 14. The absolute configurations of (-)-(2R,3S)-epoxy-3-(4-chlorophenyl)-1-phenyl-1-propanone 12 and (-)-4-chloro-(2R,3S)-epoxy- 1,3-diphenyl-1-butanone 14 have also been determined by X-ray diffraction. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4539 / 4551
页数:13
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