Steric hindrance versus asymmetric induction: new PN-ligands for carbon-carbon coupling reactions

被引：63

作者：

Bourghida, M ^{[1
]}

Widhalm, M ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 06期

基金：

奥地利科学基金会;

关键词：

D O I：

10.1016/S0957-4166(98)00073-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two new aminophosphine ligands 4 and 5 with increased steric interaction in proximity to the N-coordination site have been prepared. Their asymmetric induction in five model reactions was tested and compared to results obtained with the parent ligand 2. This resulted in improved enantioselectivity in only one case, from 5 to 68% e.e., while in all the other cases the more crowded ligands exhibited significantly lower reactivity accompanied by decreased enantioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1073 / 1083

页数：11

共 11 条

[1] HAYASHI T, 1993, CATALYTIC ASYMMETRIC, P325
[2] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC ALKYLATION WITH PHOSPHORUS-CONTAINING C-2-SYMMETRICAL CHIRAL AMINE LIGANDS
KUBOTA, H
KOGA, K
[J]. TETRAHEDRON LETTERS, 1994, 35 (36) : 6689 - 6692
[3] Kubota H, 1996, HETEROCYCLES, V42, P543
[4] ALPHA-ALKYLATION AND STEREOCHEMISTRY OF CIS-DECAHYDROQUINOLINES AND TRANS-DECAHYDROQUINOLINES MEDIATED BY THE FORMAMIDINE AND BOC ACTIVATING GROUPS - SYNTHESIS OF PUMILIOTOXIN-C
MEYERS, AI
MILOT, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 6652 - 6660
[5] ALPHA-AMINO CARBANIONS VIA FORMAMIDINES .8. ALKYLATION OF PYRROLIDINES, PIPERIDINES, AND RELATED HETEROCYCLES
MEYERS, AI
EDWARDS, PD
RIEKER, WF
BAILEY, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) : 3270 - 3276
[6] NOYORI M, 1989, MODERN SYNTHETIC MET, P115
[7] Ojima I., 2010, CATALYTIC ASYMMETRIC
[8] Asymmetric transition metal-catalyzed allylic alkylations
Trost, BM
VanVranken, DL
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 395 - 422
[9] NEW CHIRAL AMINOPHOSPHINES AND THEIR USE IN ASYMMETRIC CATALYSIS
WIMMER, P
WIDHALM, M
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (03) : 657 - 660
[10] Preparation and chromatographic separation of diastereoisomeric diaza-diphospha-macrocycles
Wimmer, P
Widhalm, M
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 106 (1-4): : 105 - 114

← 1 2 →