Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

被引：15

作者：

Gergely, I

Hegedüs, C

Szöllösy, A

Monsees, A

Riermeier, T

Bakos, J

机构：

[1] Univ Veszprem, Dept Organ Chem, H-8201 Veszprem, Hungary

[2] Hungarian Acad Sci, Res Grp Petrochem, H-8201 Veszprem, Hungary

[3] Tech Univ Budapest, Dept Gen & Analyt Chem, H-1521 Budapest, Hungary

[4] Degussa AG, Projecthause Catalyse, D-65926 Frankfurt, Germany

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 50期

关键词：

asymmetric hydrogenation; diphosphinites; rhodium; dimethyl itaconate; methyl(Z)-alpha-acetamido cinnamate;

D O I：

10.1016/j.tetlet.2003.09.217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electronic and steric effects in the rhodium diphosphinite catalyzed asymmetric hydrogenation were investigated. A series of electronically and sterically modified (S)-BINOL and (S)-H-8-BINOL ligands was synthesized and effects on the catalytic performance were studied. Phosphinite basicity was varied by using p-CH3O, p-CH3, p-H, p-CF3, 3,5-(CH3)(2), 3,5-(CF3)(2) substituents on the diphenylphosphine moieties. In the hydrogenation of dimethyl itaconate and methyl (Z)-alpha-acetamido cinnamate an increase in enantioselectivity and activity was observed with increasing phosphine basicity. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9025 / 9028

页数：4

共 34 条

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