Non-linear effects in ruthenium-catalysed asymmetric hydrogenation with atropisomeric diphosphanes

被引：0

作者：

Girard, C

Genêt, JP

Bulliard, M

机构：

[1] Ecole Natl Super Chim Paris, Lab Synth Select Organ & Prod Nat, CNRS, UMR 7573, F-75231 Paris 05, France

[2] La Croix Cadeau, PPG Sipsy, F-49242 Avrille, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 1999卷 / 11期

关键词：

nonlinear effects; asymmetric catalysis; ruthenium complexes; atropisomeric phosphanes; hydrogenation;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strong positive nonlinear effect (asymmetric amplification) was found to take place during asymmetric hydrogenations using chiral atropisomeric diphosphane-ruthenium catalysts. As an example, at atmospheric pressure the use of 50% ee BINAP to prepare [(binap)Ru(Br)(2)] give rise to a hydrogenated product with 91% ee. The influence of temperature and hydrogen pressure on this effect are presented. These nonlinear effects can be explained on the basis of a hydrogenation mechanism in which diastereomeric dimers as pre-catalytic species are present.

引用

页码：2937 / 2942

页数：6

共 42 条

[1] [Anonymous], 1996, ANGEW CHEM, DOI DOI 10.1002/ANGE.19961081506
[2] KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2]
ASHBY, MT
HALPERN, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 589 - 594
[3] Nonlinear stereochemical effects in asymmetric reactions
Avalos, M
Babiano, R
Cintas, P
Jimenez, JL
Palacios, JC
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (18) : 2997 - 3017
[4] Mathematical models of nonlinear effects in asymmetric catalysis: New insights based on the role of reaction rate
Blackmond, DG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) : 12934 - 12939
[5] Asymmetric autocatalysis with amplification of chirality
Bolm, C
Bienewald, F
Seger, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15): : 1657 - 1659
[6] Bolm C, 1996, Advanced Asymmetric Synthesis, P9
[7] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
COREY, EJ
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12579 - 12580
[8] CHIRAL POISONING IN THE KINETIC RESOLUTION OF ALLYLIC ALCOHOLS
FALLER, JW
TOKUNAGA, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7359 - 7362
[9] CHIRAL POISONING - A NOVEL STRATEGY FOR ASYMMETRIC CATALYSIS
FALLER, JW
PARR, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 804 - 805
[10] CONTROLLING STEREOCHEMISTRY IN C-C AND C-H BOND FORMATION WITH ELECTRONICALLY ASYMMETRIC ORGANOMETALLICS AND CHIRAL POISONS
FALLER, JW
MAZZIERI, MR
NGUYEN, JT
PARR, J
TOKUNAGA, M
[J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (07) : 1463 - 1469

← 1 2 3 4 5 →