New chiral 1,3-diphosphine ligands for Rh-catalyzed enantioselective hydrogenation:: a search for electronic effects

被引：25

作者：

Dubrovina, NV

Tararov, VI

Monsees, A

Spannenberg, A

Kostas, ID

Börner, A

机构：

[1] Leibniz Inst Organ Katalyse EV, D-18059 Rostock, Germany

[2] Degussa Homogeneous Catalysts, D-63457 Hanau, Wolfgang, Germany

[3] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, Athens 11635, Greece

[4] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 22期

关键词：

D O I：

10.1016/j.tetasy.2005.08.048

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New electron-rich chiral 1,3-diphosphines of the BDPP type were prepared from 1, 3-diphenylpropane- 1,3-diol by an economically feasible synthetic approach. The a-donor properties of the phosphines were determined by measurement of J(P-31-Se-77) coupling constants in the corresponding phosphine selenides. For comparison related, but electronically different, 1,3-diphosphines were considered. The new diphosphines showed good enantioselectivities as ligands in the Rh-catalyzed enantioselective hydrogenation of benchmark substrates and beta-amino acid precursors (up to 98% ee). The electronic effects on the outcome of the enantioselective catalysis have been analyzed. (c) 2005 Published by Elsevier Ltd.

引用

页码：3640 / 3649

页数：10

共 37 条

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