A CATALYTIC ENANTIOSELECTIVE MICHAEL ADDITION OF A SIMPLE MALONATE TO PROCHIRAL ALPHA,BETA-UNSATURATED KETONES AND ALDEHYDES

被引：166

作者：

YAMAGUCHI, M

SHIRAISHI, T

HIRAMA, M

机构：

[1] Department of Chemistry, Faculty of Science, Tohoku University, Sendai, 980, Aoba

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 08期

关键词：

D O I：

10.1002/anie.199311761

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomeric excesses of up to 77% ee can be achieved in the Michael addition of diisopropyl malonate to enones and enals in the presence of 5 mol% of the rubidium salt Of L-proline (which contains a small amount of water) as catalyst. The absolute configurations of the products show that the nucleophile always attacks from the same side of the C = O plane irrespective of the configuration of the C = C bond.

引用

收藏

页码：1176 / 1178

页数：3

相关论文

共 19 条

[1] ASYMMETRIC MICHAEL ADDITIONS CATALYZED BY NI(II) AND CO(II) COMPLEXES WITH HOMOCHIRAL LIGANDS [J].

BOTTEGHI, C ;

PAGANELLI, S ;

SCHIONATO, A ;

BOGA, C ;

FAVA, A .

JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (01) :7-21

[2] ASYMMETRIC CATALYSIS .65. ENANTIOSELECTIVE ALKYLATION OF ALPHA-ISOPROPYL-3,4-DIMETHOXYBENZYLCYANIDE [J].

BRUNNER, H ;

ZINTL, H .

MONATSHEFTE FUR CHEMIE, 1991, 122 (10) :841-848

[3]

DEHMLOW EV, 1992, LIEBIGS ANN CHEM, P283

[4] COPPER(II) IN ORGANIC-SYNTHESIS .8. ENANTIOSELECTIVE MICHAEL REACTIONS WITH CHIRAL COPPER(II) COMPLEXES AS CATALYSTS [J].

DESIMONI, G ;

QUADRELLI, P ;

RIGHETTI, PP .

TETRAHEDRON, 1990, 46 (08) :2927-2934

[5] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

[6]

Eder U., 1971, ANGEW CHEM, V83, P492

[7] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].

HAJOS, ZG ;

PARRISH, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621

[8] ASYMMETRIC REACTIONS OF ENAMINES WITH METHYL (E)-4-OXO-4-(2-OXO-1,3-OXAZOLIDIN-3-YL)-2-BUTENOATE BY THE USE OF A CHIRAL TITANIUM REAGENT [J].

HAYASHI, Y ;

OTAKA, K ;

SAITO, N ;

NARASAKA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) :2122-2127

[9] CATALYTIC USE OF TIN(II) REAGENTS IN ORGANIC-SYNTHESIS [J].

IWASAWA, N ;

YURA, T ;

MUKAIYAMA, T .

TETRAHEDRON, 1989, 45 (04) :1197-1207

[10] SYNTHESIS OF OPTICALLY-ACTIVE THIADECALINS AND THIAHYDRINDANS BY A PROLINE-CATALYZED INTRAMOLECULAR MICHAEL REACTION [J].

KOZIKOWSKI, AP ;

MUGRAGE, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2274-2275