CATALYTIC ASYMMETRIC ALKYLATION OF ALDEHYDES BY DIETHYLZINC IN THE PRESENCE OF N-ISO-PROPYLEPHEDRINE - DEPENDENCE OF ENANTIOSELECTIVITY ON ET2ZN-RCHO

被引：51

作者：

CHALONER, PA

LANGADIANOU, E

机构：

[1] School of Chemistry and Molecular Sciences, University of Sussex, Falmer, Brighton

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)97838-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective alkylation of a range of aldehydes by diethylzinc in the presence of N-isopropylephedrine has been investigated. Both the yield and the enantioselectivity of the reaction was found to depend on the ratio of Et2Zn to the aldehyde. © 1990.

引用

收藏

页码：5185 / 5188

页数：4

相关论文

共 14 条

[1] ASYMMETRIC REDUCTIONS .8. THE ACTION OF THE GRIGNARD REAGENT FROM (+)-1-CHLORO-2-METHYLBUTANE ON CYCLOHEXYL ALKYL KETONES [J].

BURROWS, EP ;

WELCH, FJ ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (04) :880-885

[2] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE IN THE PRESENCE OF EPHEDRINE DERIVATIVES [J].

CHALONER, PA ;

PERERA, SAR .

TETRAHEDRON LETTERS, 1987, 28 (26) :3013-3014

[3]

CHALONER PA, IN PRESS

[4] ZINC-COMPLEXES OF CHIRAL PHENOLS AS CATALYSTS FOR ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

COREY, EJ ;

HANNON, FJ .

TETRAHEDRON LETTERS, 1987, 28 (44) :5237-5240

[5] 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

[6]

JTSUNO S, 1987, J ORG CHEM, V52, P4140

[7] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].

KITAMURA, M ;

OKADA, S ;

SUGA, S ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036

[8] 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

[9]

NOYORI R, 1981, PURE APPL CHEM, V53, P2316

[10] STUDIES ON MECHANISM OF SEPARATION OF DIASTEREOISOMERIC ESTERS BY GAS-LIQUID CHROMATOGRAPHY - EFFECT OF BULK DISSYMMETRY AND DISTANCE BETWEEN OPTICAL CENTERS [J].

ROSE, HC ;

STERN, RL ;

KARGER, BL .

ANALYTICAL CHEMISTRY, 1966, 38 (03) :469-&