Synthesis of highly enantiomerically enriched planar chiral ruthenium complexes via Pd-catalysed asymmetric hydrogenolysis

被引：63

作者：

Mercier, Audrey ^{[1
]}

Yeo, Wee Chuan ^{[1
]}

Chou, Jingyu ^{[1
]}

Chaudhuri, Piyali Datta ^{[1
]}

Bernardinelli, Gerald ^{[1
]}

Kuendig, E. Peter ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 35期

基金：

瑞士国家科学基金会;

关键词：

ANTI-MARKOVNIKOV HYDRATION; ENANTIOSELECTIVE METHOXYCARBONYLATION; BENZYLIC ALCOHOL; ARENE COMPOUNDS; INDUCTION; RESOLUTION; LIGAND; IRON;

D O I：

10.1039/b910977c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Key elements in this communication are a very efficient microwave synthesis of [RuCp(naphthalene)][PF6], the precursor of [RuCp(CH3CN)(3)][PF6], and a Pd-catalysed asymmetric hydrogenolysis to afford planar chiral ruthenium complexes with high levels of enantioselectivity using a bulky chiral phosphoramidite ligand.

引用

页码：5227 / 5229

页数：3

共 46 条

[1] Microwave chemistry: Out of the kitchen [J].

Adam, D .

NATURE, 2003, 421 (6923) :571-572

[2] Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].

Arrayas, Ramon Gomez ;

Adrio, Javier ;

Carretero, Juan Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715

[3] Synthesis and Resolution of Planar-Chiral Ruthenium-Palladium Complexes with ECE′ Pincer Ligands [J].

Bonnet, Sylvestre ;

Li, Jie ;

Siegler, Maxime A. ;

von Chrzanowski, Lars S. ;

Spek, Anthony L. ;

van Koten, Gerard ;

Gebbink, Robertus J. M. Klein .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3340-3343

[4] Catalytic-enantioselective methoxycarbonylation of 1,3-dichloroarene-tricarbonyl-chromium(0) complexes:: A desymmetrization approach to planar chirality [J].

Böttcher, A ;

Schmalz, HG .

SYNLETT, 2003, (11) :1595-1598

[5] REACTIONS OF CATIONIC (ETA-6-CHLOROARENE) COMPLEXES OF IRON AND RUTHENIUM WITH SOME O-SILYL AND C-SILYL COMPOUNDS [J].

CAMBIE, RC ;

COULSON, SA ;

MACKAY, LG ;

JANSSEN, SJ ;

RUTLEDGE, PS ;

WOODGATE, PD .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 409 (03) :385-409

[6] A concise update on the applications of chiral ferrocenyl phosphines in homogeneous catalysis leading to organic synthesis [J].

Colacot, TJ .

CHEMICAL REVIEWS, 2003, 103 (08) :3101-3118

[7] An enantioselective CpRu-catalyzed Carroll rearrangement [J].

Constant, Samuel ;

Tortoioli, Simone ;

Mueller, Jessica ;

Lacour, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) :2082-2085

[8] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547

[9] Nucleophilic catalysis with π-bound nitrogen heterocycles:: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes [J].

Garrett, CE ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7479-7483

[10] 1,2,3,4-TETRAMETHYL-5-(TRIFLUOROMETHYL)CYCLOPENTADIENIDE - A UNIQUE LIGAND WITH THE STERIC PROPERTIES OF PENTAMETHYLCYCLOPENTADIENIDE AND THE ELECTRONIC-PROPERTIES OF CYCLOPENTADIENIDE [J].

GASSMAN, PG ;

MICKELSON, JW ;

SOWA, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6942-6944

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