SILVER(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF ISOCYANOACETATE

被引：110
作者：
HAYASHI, T
UOZUMI, Y
YAMAZAKI, A
SAWAMURA, M
HAMASHIMA, H
ITO, Y
机构：
[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM,KYOTO 606,JAPAN
[2] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 24期
关键词：
D O I：
10.1016/0040-4039(91)85090-R
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
High stereoselectivity (over 80% ee) was attained in silver(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with aldehydes in the presence of a chiral (aminoalkyl)ferrocenylphosphine-silver(I) complex by slow addition of the isocyanoacetate over a period of 1 h to a solution of aldehyde and the silver(I) catalyst in 1,2-dichloroethane at 30-degrees-C.
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页码：2799 / 2802
页数：4
相关论文
共 24 条
[1]  
BONATI F, 1973, GAZZ CHIM ITAL, V103, P373
[2]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE METAL-COMPLEXES [J].
HAYASHI, T .
PURE AND APPLIED CHEMISTRY, 1988, 60 (01) :7-12
[3]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES [J].
HAYASHI, T ;
MISE, T ;
FUKUSHIMA, M ;
KAGOTANI, M ;
NAGASHIMA, N ;
HAMADA, Y ;
MATSUMOTO, A ;
KAWAKAMI, S ;
KONISHI, M ;
YAMAMOTO, K ;
KUMADA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1138-1151
[4]   ASYMMETRIC-SYNTHESIS OF THREO-SPHINGOSINES AND ERYTHRO-SPHINGOSINES BY ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].
ITO, Y ;
SAWAMURA, M ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1988, 29 (02) :239-240
[5]   ASYMMETRIC ALDOL REACTION OF AN ISOCYANOACETATE WITH ALDEHYDES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES - DESIGN AND PREPARATION OF NEW EFFICIENT FERROCENYLPHOSPHINE LIGANDS [J].
ITO, Y ;
SAWAMURA, M ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1987, 28 (49) :6215-6218
[6]   CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].
ITO, Y ;
SAWAMURA, M ;
HAYASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6405-6406
[7]   ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATES WITH PARAFORMALDEHYDE CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES - CATALYTIC ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYLSERINES [J].
ITO, Y ;
SAWAMURA, M ;
SHIRAKAWA, E ;
HAYASHIZAKI, K ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1988, 29 (02) :235-238
[8]   ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-ALPHA-ALKYLAMINO ACIDS BY ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES [J].
ITO, Y ;
SAWAMURA, M ;
SHIRAKAWA, E ;
HAYASHIZAKI, K ;
HAYASHI, T .
TETRAHEDRON, 1988, 44 (17) :5253-5262
[9]   ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOACETAMIDES WITH ALDEHYDES CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE GOLD(I) COMPLEX [J].
ITO, Y ;
SAWAMURA, M ;
KOBAYASHI, M ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1988, 29 (48) :6321-6324
[10]   ASYMMETRIC ALDOL REACTION OF ALPHA-KETOESTERS WITH ISOCYANOACETATE AND ISOCYANOACETAMIDE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].
ITO, Y ;
SAWAMURA, M ;
HAMASHIMA, H ;
EMURA, T ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1989, 30 (35) :4681-4684
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