A new chiral diphosphine ligand and its asymmetric induction in catalytic hydroformylation of olefins

被引：38

作者：

Lu, SJ ^{[1
]}

Li, XD ^{[1
]}

Wang, AL ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CATALYSIS TODAY | 2000年 / 63卷 / 2-4期

基金：

中国国家自然科学基金;

关键词：

chiral diphosphine; asymmetric hydroformylation; rhodium catalyst;

D O I：

10.1016/S0920-5861(00)00500-9

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new chiral ligand, 1,6-anhydro-2,4-bis(diphenylphosphino)pyranose (ABDPP), was prepared from D-glucose. The ligand was used to prepare a chiral rhodium catalyst system for asymmetric hydroformylation of olefins. For vinyl acetate, the catalytic hydroformylation gave rather high yield (96%), high enantioselectivity (92% eel, and high regioselectivity (b/n = 95/5). But for styrene and norbornene, the results were not so good. The rather high sterioselectivity in the hydroformylation of vinyl acetate is explained in terms of the hydrogen bonding between OH group in the ligand molecule and the carbonyl group of vinyl acetate. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：531 / 536

页数：6

共 50 条

[41] Catalytic asymmetric synthesis with trans-chelating chiral diphosphine ligand TRAP. Rhodium-catalyzed asymmetric michael addition of α-cyano carboxylates
Sawamura, Massaya
Hamashima, Hitoshi
Ito, Yoshihiko
Journal of the American Chemical Society, 1992, 114 (21):
[42] Asymmetric hydroformylation catalysed by platinum complexes of new chiral bisphosphites
CserepiSzucs, S
Bakos, J
CHEMICAL COMMUNICATIONS, 1997, (06) : 635 - 636
[43] Dialkylzinc additions with a chiral osmaimidazolidine ligand from asymmetric diamination of olefins
Muñiz, K
TETRAHEDRON LETTERS, 2003, 44 (17) : 3547 - 3549
[44] A chiral diphosphine as trans-chelate ligand and its relevance to catalysis
Nasser, Nasser
Eisler, Dana J.
Puddephatt, Richard J.
CHEMICAL COMMUNICATIONS, 2010, 46 (11) : 1953 - 1955
[45] Asymmetric hydroformylation of heterocyclic olefins catalyzed by chiral phosphine-phosphite-Rh(I) complexes
Horiuchi, T
Ohta, T
Shirakawa, E
Nozaki, K
Takaya, H
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13): : 4285 - 4292
[46] ASYMMETRIC HYDROFORMYLATION OF SOME C2V OLEFINS CATALYZED BY CHIRAL RHODIUM COMPLEXES
BOTTEGHI, C
BRANCA, M
MICERA, G
PIACENTI, F
MENCHI, G
CHIMICA & L INDUSTRIA, 1978, 60 (01): : 16 - 17
[47] Synthesis of novel chiral biquinolyl diphosphine ligand and its applications in palladium-catalyzed asymmetric allylic substitution reactions
Zhang, Rui
Xie, Bin
Chen, Guo-Shu
Qiu, Liqin
Chen, Yi-Xin
TETRAHEDRON LETTERS, 2016, 57 (08) : 845 - 848
[48] Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones
Kuwano, R
Uemura, T
Saitoh, M
Ito, Y
TETRAHEDRON LETTERS, 1999, 40 (07) : 1327 - 1330
[49] SYNTHESIS OF CHIRAL TWIN CORONET PORPHYRINS AND CATALYTIC AND ASYMMETRIC EPOXIDATION OF OLEFINS
NARUTA, Y
TANI, F
MARUYAMA, K
CHEMISTRY LETTERS, 1989, (07) : 1269 - 1272
[50] Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins
J Am Chem Soc, 24 (5943-5952):

← 1 2 3 4 5 →