THE CATALYTIC ASYMMETRIC ALDOL REACTION OF SILYL KETENE ACETALS WITH ALDEHYDES IN THE PRESENCE OF A CHIRAL BORANE COMPLEX - NITROETHANE AS A HIGHLY EFFECTIVE SOLVENT FOR CATALYTIC CONDITIONS

被引:96
作者
KIYOOKA, S
KANEKO, Y
KUME, K
机构
[1] Department of Chemistry, Kochi University, Kochi, 780, Akebono-cho
关键词
CATALYTIC; ASYMMETRIC; ALDOL REACTION; CHIRAL BORANE;
D O I
10.1016/S0040-4039(00)61236-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic asymmetric aldol reaction of silyl ketene acetals with aldehydes in the presence of 20 mol % of the chiral borane reagent, prepared in situ from the p-nitrobenzenesulfonamide of (S)-valine and BH3.THF complex, gave beta-hydroxy carboxylic acid esters in good chemical yields along with excellent enantioselectivity under conditions that employ nitroethane as an effective solvent.
引用
收藏
页码:4927 / 4930
页数:4
相关论文
共 15 条
[1]   1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].
COREY, EJ ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967
[2]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[3]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .3. ERYTHRO-SELECTIVE CONDENSATIONS VIA ZIRCONIUM ENOLATES [J].
EVANS, DA ;
MCGEE, LR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2876-2878
[4]  
FURUTA K, 1991, SYNLETT, P439
[5]   CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].
FURUTA, K ;
MARUYAMA, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042
[6]   TICL4-MEDIATED REACTIONS OF THE SILYL KETENE ACETALS DERIVED FROM N-METHYLEPHEDRINE ESTERS - AN ASYMMETRIC VARIANT OF THE MUKAIYAMA REACTION [J].
GENNARI, C ;
COLOMBO, L ;
BERTOLINI, G ;
SCHIMPERNA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2754-2760
[7]   ENANTIOSELECTIVE SYNTHESIS OF THE ALPHA,ALPHA DIMETHYL-BETA-HYDROXY ACID SUBUNIT OF THE OXAZOLOMYCIN ANTIBIOTICS [J].
KENDE, AS ;
KAWAMURA, K ;
ORWAT, MJ .
TETRAHEDRON LETTERS, 1989, 30 (43) :5821-5824
[8]   ENANTIOSELECTIVE CHIRAL BORANE-MEDIATED ALDOL REACTIONS OF SILYL KETENE ACETALS WITH ALDEHYDES - NOVEL EFFECT OF THE TRIALKYLSILYL GROUP OF THE SILYL KETENE ACETAL ON THE REACTION COURSE [J].
KIYOOKA, S ;
KANEKO, Y ;
KOMURA, M ;
MATSUO, H ;
NAKANO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2276-2278
[9]   ASYMMETRIC ALDOL REACTION BETWEEN ACHIRAL SILYL ENOL ETHERS AND ACHIRAL ALDEHYDES BY USE OF A CHIRAL PROMOTER SYSTEM [J].
KOBAYASHI, S ;
UCHIRO, H ;
FUJISHITA, Y ;
SHIINA, I ;
MUKAIYAMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4247-4252
[10]   STEREOSELECTIVE ALDOL CONDENSATION - USE OF CHIRAL BORON ENOLATES [J].
MASAMUNE, S ;
CHOY, W ;
KERDESKY, FAJ ;
IMPERIALI, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1566-1568