Chiral monodentate phosphoramidite ligands control the absolute configuration at pseudotetrahedral ruthenium: asymmetric catalytic cyclopropanation of olefins

被引：22

作者：

Huber, D ^{[1
]}

Mezzetti, A ^{[1
]}

机构：

[1] ETH Honggerberg, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 14期

关键词：

D O I：

10.1016/j.tetasy.2004.05.040

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Piano-stool ruthenium complexes of the type [RUCl2(p-cymene)(L)] (L = chiral phosphoramidite ligand) catalyse the asymmetric cyclopropanation of styrene and alpha-methylstyrene with ethyl diazoacetate after activation with TIPF6 or (Et3O)PF6 as halide scavengers. With alpha-methylstyrene, good enantioselectivities were observed (up to 86% and 87% ee for the cis- and trans-cyclopropane derivative, respectively). However, total yields and diastereoselectivities were generally low. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2193 / 2197

页数：5

共 53 条

[1] (η6-arene)ruthenium(II) complexes containing enantiomerically pure (β-aminoalkyl)phosphines or a (β-aminoalkyl) phosphinite:: synthesis, stereochemical and kinetic studies
Arena, CG
Calamia, S
Faraone, F
Graiff, C
Tiripicchio, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (18): : 3149 - 3157
[2] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects
Arnold, LA
Imbos, R
Mandoli, A
de Vries, AHM
Naasz, R
Feringa, BL
[J]. TETRAHEDRON, 2000, 56 (18) : 2865 - 2878
[3] Cis-selective asymmetric cyclopropanation of olefins catalyzed by five-coordinate [RuCl(PNNP)]+ complexes
Bachmann, S
Furler, M
Mezzetti, A
[J]. ORGANOMETALLICS, 2001, 20 (10) : 2102 - 2108
[4] Bachmann S, 2001, HELV CHIM ACTA, V84, P3063, DOI 10.1002/1522-2675(20011017)84:10<3063::AID-HLCA3063>3.0.CO
[5] 2-R
[6] Half-sandwich ruthenium(II) catalysts for C-C coupling reactions between alkenes and diazo compounds
Baratta, W
Herrman, WA
Kratzer, RM
Rigo, P
[J]. ORGANOMETALLICS, 2000, 19 (18) : 3664 - 3669
[7] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE
BENNETT, MA
SMITH, AK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02): : 233 - 241
[8] Recent advances in the chemistry of arene complexes of ruthenium(0) and ruthenium(II)
Bennett, MA
[J]. COORDINATION CHEMISTRY REVIEWS, 1997, 166 : 225 - 254
[9] Application of NOE and PGSE NMR methodologies to investigate non-covalent intimate inorganic adducts in solution
Binotti, B
Macchioni, A
Zuccaccia, C
Zuccaccia, D
[J]. COMMENTS ON INORGANIC CHEMISTRY, 2002, 23 (06) : 417 - 450
[10] High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites
Boiteau, JG
Minnaard, AJ
Feringa, BL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9481 - 9484

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