TRICARBONYL(BENZALDEHYDE)CHROMIUM(0) COMPLEXES IN ORGANIC-SYNTHESIS - A HIGHLY STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION OF CHROMIUM(0)-COMPLEXED NITRONES

被引:30
作者
MUKAI, C [1 ]
CHO, WJ [1 ]
KIM, IJ [1 ]
HANAOKA, M [1 ]
机构
[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA,ISHIKAWA 920,JAPAN
关键词
D O I
10.1016/S0040-4039(00)97200-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,3-dipolar cycloaddition of chromium(0)-complexed nitrones (10, 11) with electron-rich olefins (2) provided, after decomplexation with CAN, cis-3,5-disubstituted isoxazolidines (cis-14, 15) in a highly stereoselective as well as regioselective manner. © 1990.
引用
收藏
页码:6893 / 6896
页数:4
相关论文
共 12 条
[1]  
Confalone P. N., 1988, ORG REACTIONS, V36, P1
[2]   ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BENZYL ALCOHOLS VIA THE STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO HOMOCHIRAL TRICARBONYL(ETA-6-O-TRIALKYLSILYLBENZALDEHYDE)CHROMIUM(O) COMPLEXES [J].
DAVIES, SG ;
GOODFELLOW, CL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :393-407
[3]   NITRONE CYCLO-ADDITIONS - AN EFFICIENT METHOD FOR THE HOMOLOGATION OF ALDEHYDES TO ALPHA,BETA-UNSATURATED ALDEHYDES [J].
DESHONG, P ;
LEGINUS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (18) :3421-3423
[4]  
DeShong P., 1988, ADV CYCLOADDITION, V1, P87
[5]   REACTIONS AT HIGH-PRESSURES - [3+2] DIPOLAR CYCLOADDITION OF NITRONES WITH VINYL ETHERS [J].
DICKEN, CM ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2047-2051
[6]   1,3-DIPOLAR CYCLOADDITIONS .41. ADDITION OF NITRONES TO STYRENE - ORIENTATION AND SPATIAL RESULTS [J].
HUISGEN, R ;
GRASHEY, R ;
HAUCK, H ;
SEIDL, H .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (07) :2548-&
[7]   A HIGHLY ERYTHRO SELECTIVE ALDOL REACTION BETWEEN CHROMIUM-COMPLEXED BENZALDEHYDE DERIVATIVES AND CYCLIC SILYL ENOL ETHERS [J].
MUKAI, C ;
CHO, WJ ;
HANAOKA, M .
TETRAHEDRON LETTERS, 1989, 30 (52) :7435-7438
[8]  
MUKAI C, UNPUB
[9]   ETA-5-CYCLOHEXADIENYLTRICARBONYLCHROMIUM(0) COMPLEXES FROM ADDITION OF CARBON NUCLEOPHILES TO "ETA-6-BENZENETRICARBONYLCHROMIUM(0) - FORMATION, CHEMICAL AND SPECTROSCOPIC FEATURES, AND X-RAY-DIFFRACTION ANALYSIS [J].
SEMMELHACK, MF ;
HALL, HT ;
FARINA, R ;
YOSHIFUJI, M ;
CLARK, G ;
BARGAR, T ;
HIROTSU, K ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) :3535-3544
[10]  
TORSSELL KBG, 1987, NITRILE OXIDES NITRO