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

被引:91
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
相关论文
共 40 条
[1]   SYNTHESIS, COMPLEXING PROPERTIES AND APPLICATIONS IN ASYMMETRIC-SYNTHESIS OF BIS-LACTO-18-CROWN-6 COMPOUNDS [J].
ALONSOLOPEZ, M ;
JIMENEZBARBERO, J ;
MARTINLOMAS, M ;
PENADES, S .
TETRAHEDRON, 1988, 44 (05) :1535-1543
[2]  
AOKI S, 1992, HETEROCYCLES, V33, P493
[3]   Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions [J].
Arai, S ;
Shioiri, T .
TETRAHEDRON LETTERS, 1998, 39 (15) :2145-2148
[4]   Phase-transfer-catalyzed asymmetric Darzens reaction [J].
Arai, S ;
Shirai, Y ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON, 1999, 55 (20) :6375-6386
[5]   Novel monoaza- and diazacrown ethers incorporating sugar units and their extraction ability towards picrate salts [J].
Bako, P ;
Toke, L .
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1995, 23 (03) :195-201
[6]  
BAKO P, 1982, ACTA CHIM HUNG, V111, P297
[7]  
BAKO P, 1981, LIEBIGS ANN CHEM, P1163
[8]   D-glucose-based azacrown ethers with a phosphonoalkyl side chain:: application as enantioselective phase transfer catalysts [J].
Bakó, P ;
Novák, T ;
Ludányi, K ;
Pete, B ;
Toke, L ;
Keglevich, G .
TETRAHEDRON-ASYMMETRY, 1999, 10 (12) :2373-2380
[9]  
BAKO P, 1990, LIEBIGS ANN CHEM, P1161
[10]   CLEAVAGE OF THE ACETAL RINGS IN BIS(METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDO)-18-CROWN-6 [J].
BAKO, P ;
FENICHEL, L ;
TOKE, L ;
TOTH, G .
CARBOHYDRATE RESEARCH, 1986, 147 (01) :31-37