Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalysed allylic substitution

被引：75

作者：

Chesney, A ^{[1
]}

Bryce, MR ^{[1
]}

Chubb, RWJ ^{[1
]}

Batsanov, AS ^{[1
]}

Howard, JAK ^{[1
]}

机构：

[1] UNIV DURHAM,DEPT CHEM,DURHAM DH1 3LE,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(97)00246-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The syntheses of novel ferrocene-based chiral oxazolines 17, 18 and 26 are reported. The application of these compounds as catalysts for asymmetric palladium-catalysed allylic substitution reactions has been investigated. These reactions afford the substitution products in both high yield and high enantiomeric excess. The solution electrochemical redox-behaviour of 17, 18 and 26 in the presence of palladium ions establishes that palladium coordination to the oxazoline results in a significant anodic shift in the redox potential of the ferrocene ligand. The X-ray crystal structure of the ferrocene-hydroxy amide derivative 16 is also reported. (C) 1997 Elsevier Science Ltd.

引用

页码：2337 / 2346

页数：10

共 51 条

[1] PREPARATION AND CRYSTAL-STRUCTURES OF (1,1'-RUTHENOCENEDITHIOLATO-S,S',RU)(TRIPHENYLPHOSPHINE)-NICKEL(II) AND (1,1'-METALLOCENEDIOXALATO-O,O',FE(OR RU))(TRIPHENYLPHOSPHINE)PALLADIUM(II) - THE METAL (FE OR RU)-METAL (PD OR NI) DATIVE BOND
AKABORI, S
KUMAGAI, T
SHIRAHIGE, T
SATO, S
KAWAZOE, K
TAMURA, C
SATO, M
[J]. ORGANOMETALLICS, 1987, 6 (10) : 2105 - 2109
[2] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS
ALLEN, JV
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
COOTE, SJ
[J]. TETRAHEDRON, 1994, 50 (03) : 799 - 808
[3] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS
ALLEN, JV
COOTE, SJ
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2065 - 2072
[4] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION - ELECTRONIC AND STERIC EFFECTS OF THE LIGAND
ALLEN, JV
BOWER, JF
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 1895 - 1898
[5] DERIVATIVES OF DICYCLOPENTADIENYLIRON
ARIMOTO, FS
HAVEN, AC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) : 6295 - 6297
[6] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES
AUBURN, PR
MACKENZIE, PB
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2033 - 2046
[7] Beer PD, 1995, NATO ADV SCI INST SE, V456, P99
[8] BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS
BOLM, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05): : 542 - 543
[9] BOSNICH B, 1986, NATO ASI SERIES 6, V103, pCH3
[10] Chiral oxazolines linked to tetrathiafulvalene (TTF): Redox-active ligands for asymmetric synthesis
Chesney, A
Bryce, MR
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (11) : 3247 - 3254

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