Enantioselective and regioselective ruthenium-catalyzed decarboxylative etherification of allyl aryl carbonates

被引：53

作者：

Austeri, Martina ^{[1
]}

Linder, David ^{[1
]}

Lacour, Jerome ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 19期

关键词：

allylic compounds; C-O bond formation; enantioselectivity; N ligands; ruthenium;

D O I：

10.1002/chem.200800619

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to investigate enantioselective and regioselective ruthenium-catalyzed decarboxylative etherification of allyl aryl carbonates. It was observed that allyl aryl carbonates react in the presence of CpRu and pyridylmonooxazoline ligands, to produced branched allyl aryl ethers in high enantiomeric purity and significant regioselectivity. The transformation demonstrated an effective enantioselective decarboxylative etherification. Initial investigations were conducted, using conditions similar to that of the enantioselective rearrangement of allyl β-keto esters. Allyl carbonate was treated with catalytic amounts of CpRu in THF at room temperature. The scope of the asymmetric protocol was also studied with allyl carbonates, with improved conditions.

引用

页码：5737 / 5741

页数：5

共 89 条

[11]

Constant S., 2007, ANGEW CHEM, V119, P9137

[12]

Constant S., 2007, ANGEW CHEM, V119, P2128

[13] Air- and microwave-stable (C5H5)Ru catalysts for improved regio and enantioselective carroll rearrangements [J].

Constant, Samuel ;

Tortoioli, Simone ;

Mueller, Jessica ;

Linder, David ;

Buron, Frederic ;

Lacour, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) :8979-8982

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

Constant, Samuel ;

Tortoioli, Simone ;

Mueller, Jessica ;

Lacour, Jerome .

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

[15] Cp*Rh complexes with pyridyloxazolines: synthesis, fluxionality and applications as asymmetric catalysts for Diels-Alder reactions [J].

Davies, DL ;

Fawcett, J ;

Garratt, SA ;

Russell, DR .

DALTON TRANSACTIONS, 2004, (21) :3629-3634

[16] (Arene)ruthenium complexes with bis(oxazolines): Synthesis and applications as asymmetric catalysts for Diels-Alder reactions [J].

Davies, DL ;

Fawcett, J ;

Garratt, SA ;

Russell, DR .

ORGANOMETALLICS, 2001, 20 (14) :3029-3034

[17] Synthesis and reactivity of [Ru(Cp*)(L)(MeCN)2][PF6] (L = Ph2POMe or Ph2P-o-tolyl) and {Ru(Cp*)[Ph2PCH2C(tBu)=O](MeCN)}[PF6] complexes, their involvement as catalyst precursors for regioselective allylic substitution reactions and related [Ru(Cp*)Cl(Ph2POMe)(RCHCHCH2)][PF6] η3-allyl ruthenium(IV) intermediates [J].

Demerseman, B ;

Renaud, JL ;

Toupet, L ;

Hubert, C ;

Bruneau, C .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (07) :1371-1380

[18] Model intermolecular asymmetric Heck reactions catalyzed by chiral pyridyloxazoline palladium(II) complexes [J].

Dodd, David W. ;

Toews, Heather E. ;

Carneiro, Florentino d. S. ;

Jennings, Michael C. ;

Jones, Nathan D. .

INORGANICA CHIMICA ACTA, 2006, 359 (09) :2850-2858

[19] Regio- and enantiospecific rhodium-catalyzed allylic etherification reactions using copper(I) alkoxides: Influence of the copper halide salt on selectivity [J].

Evans, PA ;

Leahy, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7882-7883

[20] Regioselective and enantiospecific rhodium-catalyzed intermolecular allylic etherification with ortho-substituted phenols [J].

Evans, PA ;

Leahy, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :5012-5013

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