Dramatic reversal of enantioselection in a palladium catalysed allylic substitution by choice of nitrogen substituents in a N-P chiral ligand

被引：37

作者：

Anderson, JC ^{[1
]}

Cubbon, RJ

Harling, JD

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(99)00298-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two chiral chelate nitrogen-phosphorus ligands derived from (S)-valine, with the potential for stereogenic nitrogen donors, gave dramatically different enantioselectivities, ranging from 92% ee (R) to 83% ee (S), in the palladium catalysed allylic substitution reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2829 / 2832

页数：4

共 26 条

[1] ADAMS H, UNPUB
[2] AKERMARK B, 1984, ORGANOMETALLICS, V3, P679
[3] AKERMARK B, 1987, ORGANOMETALLICS, V6, P620
[4] AKERMARK B, 1990, J AM CHEM SOC, V112, P4587
[5] Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
Anderson, JC
Cubbon, R
Harding, M
James, DS
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (19) : 3461 - 3490
[6] Sulfur-imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation
Anderson, JC
James, DS
Mathias, JP
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 753 - 756
[7] New chiral N,S-ligands based on oxazoline-thioglucose donors. Palladium(II)-catalyzed enantioselective allylic alkylation
Boog-Wick, K
Pregosin, PS
Trabesinger, G
[J]. ORGANOMETALLICS, 1998, 17 (15) : 3254 - 3264
[8] PHOSPHINE-BORANE COMPLEXES - DIRECT USE IN ASYMMETRIC CATALYSIS
BRISSET, H
GOURDEL, Y
PELLON, P
LECORRE, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (28) : 4523 - 4526
[9] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE
BROWN, JM
HULMES, DI
GUIRY, PJ
[J]. TETRAHEDRON, 1994, 50 (15) : 4493 - 4506
[10] SYNTHESIS AND STRUCTURE OF PYRAZOLE-CONTAINING FERROCENYL LIGANDS FOR ASYMMETRIC CATALYSIS
BURCKHARDT, U
HINTERMANN, L
SCHNYDER, A
TOGNI, A
[J]. ORGANOMETALLICS, 1995, 14 (11) : 5415 - 5425

← 1 2 3 →