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

[1] Enantioselective Heck-type reaction catalyzed by tropos-Pd(II) complex with chiraphos ligand [J].

Akiyama, K ;

Wakabayashi, K ;

Mikami, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1569-1575

[2]

[Anonymous], ANGEW CHEM

[3] SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX [J].

BOLM, C ;

WEICKHARDT, K ;

ZEHNDER, M ;

RANFF, T .

CHEMISCHE BERICHTE, 1991, 124 (05) :1173-1180

[4]

Braun M., 2006, ANGEW CHEM, V118, P7106

[5] Tsuji-Trost allylic alkylation with ketone enolates [J].

Braun, Manfred ;

Meier, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :6952-6955

[6] Pentamethylcyclopentadienyl-ruthenium catalysts for regio- and enantioselective allylation of nucleophiles [J].

Bruneau, Christian ;

Renaud, Jean-Luc ;

Demerseman, Bernard .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5178-5187

[7] Optically active transition metal complexes. 129. Novel cycloheptatrienyl-molybdenum and cyclopentadienyl-ruthenium complexes with chiral pyridinecarbaldiminato chelate ligands: Syntheses, molecular structures, properties, and stereochemistry at the metal atom [J].

Brunner, H ;

Klankermayer, J ;

Zabel, M .

ORGANOMETALLICS, 2002, 21 (26) :5746-5756

[8] Ruthenium-catalyzed stereospecific decarboxylative allylation of non-stabilized ketone enolates [J].

Burger, EC ;

Tunge, JA .

CHEMICAL COMMUNICATIONS, 2005, (22) :2835-2837

[9] Ruthenium-catalyzed decarboxylative allylation of nonstabilized ketone enolates [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (15) :2603-2605

[10] ENANTIOSELECTIVE CARBON-DIOXIDE EXTRUSION FROM ALLYL PHENYL CARBONATES BY NICKEL, PALLADIUM AND RHODIUM CATALYSTS [J].

CONSIGLIO, G ;

SCALONE, M ;

RAMA, F .

JOURNAL OF MOLECULAR CATALYSIS, 1989, 50 (02) :L11-L15

← 1 2 3 4 5 6 7 8 9 →