ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALPHA-BRANCHED ALDEHYDES

被引：131

作者：

KANG, J

LEE, JW

KIM, JI

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 17期

关键词：

D O I：

10.1039/c39940002009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of diethylzinc with alpha-branched aldehydes in the presence of a catalytic amount of (1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol 1 provided the corresponding secondary alcohols in almost 100% enantiomeric excess.

引用

页码：2009 / 2010

页数：2

共 19 条

[1] ELECTRONIC EFFECTS IN STEREOCHEMISTRY .3. ASYMMETRIC REDUCTION OF PHENYLALKYLKETONES DIVERSELY SUBSTITUTED BY CHIRAL AROMATIC ORGANOMAGNESIUM COMPOUNDS [J].

CAPILLON, J ;

GUETTE, JP .

TETRAHEDRON, 1979, 35 (15) :1817-1820

[2]

HONES GB, 1993, TETRAHEDRON-ASYMMETR, V4, P261

[3] 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

[4] 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

[5]

NATSUMOTO Y, 1993, TETRAHEDRON-ASYMMETR, V4, P1763

[6] ASYMMETRIC-SYNTHESIS USING CHIRAL PIPERAZINES .3. ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ARYL ALDEHYDES CATALYZED BY CHIRAL PIPERAZINES [J].

NIWA, S ;

SOAI, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2717-2720

[7] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].

NOYORI, R ;

KITAMURA, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69

[8] 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

[9] ASYMMETRIC AMPLIFYING PHENOMENA IN ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].

OGUNI, N ;

MATSUDA, Y ;

KANEKO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7877-7878

[10]

RICHARD RH, 1914, J CHEM SOC, P1115

← 1 2 →