ENANTIOSELECTIVE PHENYLATION OF PROCHIRAL ALDEHYDES USING A KINETICALLY FORMED CHIRAL COMPLEX BETWEEN GRIGNARD ZINC HALIDE REAGENT AND N,N-DIBUTYL-NOREPHEDRINE

被引：48

作者：

SOAI, K

KAWASE, Y

OSHIO, A

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Shinjuku

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期

关键词：

D O I：

10.1039/p19910001613

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active phenylmethanols have been synthesized in good to high enantiomeric excess (up to 82% e.e.) by the enantioselective addition of a kinetically formed complex (between phenyl Grignard-zinc halide and N,N-dibutylnorephedrine) to aliphatic, aromatic and alpha,beta-unsaturated aldehydes.

引用

页码：1613 / 1615

页数：3

共 18 条

[1] CATALYTIC ASYMMETRIC ALKYLATION OF ALDEHYDES BY DIETHYLZINC IN THE PRESENCE OF N-ISO-PROPYLEPHEDRINE - DEPENDENCE OF ENANTIOSELECTIVITY ON ET2ZN-RCHO
CHALONER, PA
LANGADIANOU, E
[J]. TETRAHEDRON LETTERS, 1990, 31 (36) : 5185 - 5188
[2] ZINC-COMPLEXES OF CHIRAL PHENOLS AS CATALYSTS FOR ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES
COREY, EJ
HANNON, FJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (44) : 5237 - 5240
[3] HUBSCHER J, 1990, HELV CHIM ACTA, V73, P1068, DOI 10.1002/hlca.19900730431
[4] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY POLYMER-SUPPORTED CHIRAL AMINO-ALCOHOLS - EVIDENCE FOR A 2 ZINC SPECIES MECHANISM
ITSUNO, S
FRECHET, JMJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4140 - 4142
[5] CHIRAL OXAZABOROLIDINES AS CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
JOSHI, NN
SREBNIK, M
BROWN, HC
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5551 - 5554
[6] CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES
KITAMURA, M
SUGA, S
KAWAI, K
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 6071 - 6072
[7] CHIRAL CATALYSIS OF ADDITIONS OF ALKYLLITHIUMS TO ALDEHYDES
MAZALEYRAT, JP
CRAM, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) : 4585 - 4586
[8] MORRISON JD, 1984, ASYMMETRIC SYNTHESIS
[9] 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
MUKAIYAMA, T
SOAI, K
SATO, T
SHIMIZU, H
SUZUKI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) : 1455 - 1460
[10] ASYMMETRIC AMPLIFYING PHENOMENA IN ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE
OGUNI, N
MATSUDA, Y
KANEKO, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7877 - 7878

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