STEREOSELECTIVE ADDITION-REACTION OF DIETHYLZINC TO ALDEHYDES, CATALYZED BY CINCHONA ALKALOIDS

被引:121
作者
SMAARDIJK, AA [1 ]
WYNBERG, H [1 ]
机构
[1] STATE UNIV GRONINGEN, DEPT ORGAN CHEM, NIJENBORGH 16, 9747 AG GRONINGEN, NETHERLANDS
关键词
D O I
10.1021/jo00377a024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cinchona alkaloid catalyzed reaction of diethylzinc and aldehydes leads to optically active alcohols having enantiomeric excesses up to 92%.
引用
收藏
页码:135 / 137
页数:3
相关论文
共 16 条
[1]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[2]   ENANTIOSELECTIVE ADDITION OF N-BUTYLLITHIUM TO BENZALDEHYDE IN THE PRESENCE OF CHIRAL LITHIUM AMIDES [J].
ELEVELD, MB ;
HOGEVEEN, H .
TETRAHEDRON LETTERS, 1984, 25 (45) :5187-5190
[3]   SIMPLE P-31 NMR METHOD FOR THE DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS NOT REQUIRING CHIRAL AUXILIARY COMPOUNDS [J].
FERINGA, BL ;
SMAARDIJK, A ;
WYNBERG, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) :4798-4799
[4]   CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].
KITAMURA, M ;
SUGA, S ;
KAWAI, K ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072
[5]   NOVEL TRANSITION-METAL COMPLEXES OF CAMPHORQUINONE DIOXIME LIGANDS [J].
MA, MS ;
ANGELICI, RJ .
INORGANIC CHEMISTRY, 1980, 19 (02) :363-370
[6]   CHIRAL CATALYSIS OF ADDITIONS OF ALKYLLITHIUMS TO ALDEHYDES [J].
MAZALEYRAT, JP ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4585-4586
[7]   ENANTIOFACE-DIFFERENTIATING (ASYMMETRIC) ADDITION OF ALKYLLITHIUM AND DIALKYLMAGNESIUM TO ALDEHYDES BY USING (2S,2'S)-2-HYDROXYMETHYL-1-[(1-ALKYLPYRROLIDIN-2-YL)-METHYL]PYRROLIDINES AS CHIRAL LIGANDS [J].
MUKAIYAMA, T ;
SOAI, K ;
SATO, T ;
SHIMIZU, H ;
SUZUKI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1455-1460
[8]  
NAKAMURA A, 1979, J CHEM SOC DALTON, P488, DOI 10.1039/dt9790000488
[9]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE CATALYZED BY A SMALL AMOUNT OF CHIRAL 2-AMINO-1-ALCOHOLS [J].
OGUNI, N ;
OMI, T .
TETRAHEDRON LETTERS, 1984, 25 (26) :2823-2824
[10]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ARYLALDEHYDES CATALYZED BY CHIRAL COBALT(II) AND PALLADIUM(II) COMPLEXES [J].
OGUNI, N ;
OMI, T ;
YAMAMOTO, Y ;
NAKAMURA, A .
CHEMISTRY LETTERS, 1983, (06) :841-842