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 [J].

Arena, CG ;

Calamia, S ;

Faraone, F ;

Graiff, C ;

Tiripicchio, A .

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 [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[3] Cis-selective asymmetric cyclopropanation of olefins catalyzed by five-coordinate [RuCl(PNNP)]+ complexes [J].

Bachmann, S ;

Furler, M ;

Mezzetti, A .

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 [J].

Baratta, W ;

Herrman, WA ;

Kratzer, RM ;

Rigo, P .

ORGANOMETALLICS, 2000, 19 (18) :3664-3669

[7] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].

BENNETT, MA ;

SMITH, AK .

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) [J].

Bennett, MA .

COORDINATION CHEMISTRY REVIEWS, 1997, 166 :225-254

[9] Application of NOE and PGSE NMR methodologies to investigate non-covalent intimate inorganic adducts in solution [J].

Binotti, B ;

Macchioni, A ;

Zuccaccia, C ;

Zuccaccia, D .

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 [J].

Boiteau, JG ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9481-9484

← 1 2 3 4 5 6 →