INFLUENCE OF DIFFERENT TYPES OF AMPHIPHILES ON THE RHODIUM(I) COMPLEX-CATALYZED ASYMMETRIC HYDROGENATION OF (Z)-METHYL-ALPHA-ACETAMIDOCINNAMATE IN AQUEOUS-MEDIUM

被引：78

作者：

GRASSERT, I ^{[1
]}

PAETZOLD, E ^{[1
]}

OEHME, G ^{[1
]}

机构：

[1] UNIV ROSTOCK EV,INST ORGAN KATALYSEFORSCH,BUCHBINDERSTR 5-6,O-2500 ROSTOCK,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(01)81829-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The homogeneous asymmetric hydrogenation of (Z)-methyl-alpha-acetamidocinnamate catalyzed by the system [Rh(COD)2]BF4 + 1.1 BPPM could be effected in water as medium in the presence of micelle-forming amphiphiles. Both activity and enantioselectivity were enhanced significantly and have been compared with results obtained in methanol as solvent. The effect was found with nonionic, zwitterionic and anionic surfactants and depends on the critical micelle concentration. Cationic surfactants like hexadecylalkyl ammonium salts act according to the anion as inhibitor (e.g. bromide), or promotor (e.g. hydrogensulfate). The principle of enhancing activity and stereoselectivity in complex-catalyzed hydrogenation due to micelles seems to be a phenomenon of general importance.

引用

页码：6605 / 6612

页数：8

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