New developments in the synthesis of heterotopic atropisomeric diphosphines via diastereoselective aryl coupling reactions

被引：25

作者：

Madec, J ^{[1
]}

Michaud, G ^{[1
]}

Genêt, JP ^{[1
]}

Marinetti, A ^{[1
]}

机构：

[1] ENSCP, UMR 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 14期

关键词：

D O I：

10.1016/j.tetasy.2004.05.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The new heterotopic atropisomeric diphosphine (R)-5,6-benzo-2,2'-bis(diphenylphosphino)-4',5',6'-trimethylbiphenyl has been prepared. The key step of this synthesis is a diastereoselective intramolecular aryl-aryl coupling reaction via oxidation of a suitable, chiral diarylcuprate. The catalytic properties of the diphosphine in ruthenium promoted hydrogenations of model substrates and in rhodium promoted 1,4-additions of boronic acids to alpha,beta-unsaturated ketones are fully comparable to those of reference ligands such as BINAP. This seems to indicate that C-2-symmetry is not a structural prerequisite for atropisomeric chiral diphosphines to obtain high enantio selectivities in 1,4-addition reactions as well as in hydrogenation reactions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2253 / 2261

页数：9

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