ENANTIOSELECTIVE SYNTHESIS OF 2-ISOXAZOLINES VIA ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDE TO ACHIRAL ALLYL ALCOHOL

被引:70
作者
UKAJI, Y
SADA, K
INOMATA, K
机构
关键词
D O I
10.1246/cl.1993.1847
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric 1,3-dipolar cycloaddition of a nitrile oxide to an achiral allyl alcohol was achieved by the use of (R,R)-diisopropyl tartrate as a chiral auxiliary. Treatment of the allyl alcohol with diethylzinc and the tartrate, followed by the addition of diethylzinc and a hydroximoyl chloride, afforded the corresponding (R)-2-isoxazolines with excellent enantioselectivity.
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页码:1847 / 1850
页数:4
相关论文
共 16 条
[1]  
AIKYAMA T, 1991, TETRAHEDRON LETT, V33, P5763
[2]  
CARRUTHERS W, 1990, CYCLOADDITION REACTI, P285
[3]   NEW CHIRAL AUXILIARIES FOR THERMAL CYCLOADDITIONS [J].
CURRAN, DP ;
JEONG, KS ;
HEFFNER, TA ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9238-9240
[4]   THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES - A MODEL FOR ASYMMETRIC INDUCTION IN THE NON LEWIS ACID-CATALYZED REACTIONS OF OPPOLZERS CHIRAL SULTAM [J].
CURRAN, DP ;
KIM, BH ;
DAUGHERTY, J ;
HEFFNER, TA .
TETRAHEDRON LETTERS, 1988, 29 (29) :3555-3558
[5]   REGIOCONTROL OF NITRILE OXIDE CYCLOADDITIONS TO ALLYL ALCOHOLS - SYNTHESIS OF 4-SUBSTITUTED AND 4,4-DISUBSTITUTED 5-HYDROXYMETHYL-2-ISOXAZOLINES [J].
KANEMASA, S ;
NISHIUCHI, M ;
WADA, E .
TETRAHEDRON LETTERS, 1992, 33 (10) :1357-1360
[6]   GENERATION OF NITRILE OXIDES THROUGH O-METALATION OF HYDROXIMOYL CHLORIDES - CHELATION-CONTROLLED SYN-SELECTIVE CYCLOADDITION OF NITRILE OXIDES TO ALPHA-SUBSTITUTED ALLYL ALCOHOLS [J].
KANEMASA, S ;
KOBAYASHI, S ;
NISHIUCHI, M ;
YAMAMOTO, H ;
WADA, E .
TETRAHEDRON LETTERS, 1991, 32 (44) :6367-6370
[7]   HIGHLY LK-SELECTIVE ASYMMETRIC NITRILE OXIDE CYCLOADDITIONS TO A C-2-SYMMETRICAL 1,3-DIACRYLOYL-2,2-DIMETHYLIMIDAZOLIDINE AND 4-CHIRAL 3-ACRYLOYL-2,2-DIALKYLOXAZOLIDINES [J].
KANEMASA, S ;
ONIMURA, K .
TETRAHEDRON, 1992, 48 (40) :8645-8658
[8]   2,2-DIMETHYL-4-PHENYLOXAZOLIDINE AND 2,2-DIMETHYL-4,5-DIPHENYLIMIDAZOLIDINE AS NEW CHIRAL AUXILIARIES - APPLICATIONS TO ASYMMETRIC NITRILE OXIDE CYCLOADDITIONS [J].
KANEMASA, S ;
ONIMURA, K ;
WADA, E ;
TANAKA, J .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1185-1188
[9]  
KANEMASA S, 1992, YUKI GOESI KAGAKU KO, V50, P808
[10]   A CONVENIENT SYNTHESIS OF BENZOHYDROXIMOYL CHLORIDES AS NITRILE OXIDE PRECURSORS BY HCL/N,N-DIMETHYLFORMAMIDE OXONE SYSTEM [J].
KIM, JN ;
RYU, EK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6649-6650