Thioureas as new chiral ligands for the asymmetric hydroformylation of styrene with rhodium(I) catalysts

被引：31

作者：

Breuzard, JAJ ^{[1
]}

Tommasino, ML ^{[1
]}

Touchard, F ^{[1
]}

Lemaire, M ^{[1
]}

Bonnet, MC ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, Inst Rech Catalyse, Lab Catalyse & Synth Organ, F-69626 Villeurbanne, France

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2000年 / 156卷 / 1-2期

关键词：

asymmetric catalysis; enantioselective hydroformylation; rhodium(I); styrene; chiral thioureas;

D O I：

10.1016/S1381-1169(99)00401-X

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Various new chiral thioureas have been synthesized and used as ligands for the asymmetric hydroformylation of styrene catalyzed by rhodium(I) complexes. The best results were obtained with N-phenyl-N'-(S)-(1-phenylethyl)-thiourea associated to a cationic rhodium(I) precursor, and asymmetric induction of 40% was then achieved. As enantioselectivity is obtained with low conversions, various parameters have been examined in order to increase the catalytic activity without the loss of asymmetric induction. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：223 / 232

页数：10

共 31 条

[1] ASYMMETRIC HYDROFORMYLATION [J].

AGBOSSOU, F ;

CARPENTIER, JF ;

MORTREAUX, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2485-2506

[2]

Alexakis A, 1998, SYNLETT, P873

[3]

Alexakis A, 1998, SYNLETT, P875

[4] Mixed phosphito-phosphonato rhodium(I) complexes [J].

Arena, CG ;

Nicolo, F ;

Drommi, D ;

Bruno, G ;

Faraone, F .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (23) :4357-4363

[5] Chiral cooperativity in diastereomeric diphosphite ligands: Effects on the rhodium-catalyzed enantioselective hydroformylation of styrene [J].

Buisman, GJH ;

vanderVeen, LA ;

Klootwijk, A ;

deLange, WGJ ;

Kamer, PCJ ;

vanLeeuwen, PWNM ;

Vogt, D .

ORGANOMETALLICS, 1997, 16 (13) :2929-2939

[6] Synthesis of rhodium(I) complexes with the new dithiol chiral ligand (+)-trans-2,3-bis(mercaptomethyl)-bicyclo[2.2.2]octane (H2BCOS) - Their application as catalysts precursors in the styrene hydroformylation [J].

CastellanosPaez, A ;

Castillon, S ;

Claver, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 539 (1-2) :1-7

[7] Anchoring rhodium(I) on thiourea-functionalized silica xerogels and silsesquioxanes .2. Matrix effects on the selectivity in the hydroformylation of styrene [J].

Cauzzi, D ;

Costa, M ;

Gonsalvi, L ;

Pellinghelli, MA ;

Predieri, G ;

Tiripicchio, A ;

Zanoni, R .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 541 (1-2) :377-389

[8] ANCHORING RHODIUM(I) ON BENZOYLTHIOUREA-FUNCTIONALIZED SILICA XEROGELS - PRODUCTION OF RECYCLABLE HYDROFORMYLATION CATALYSTS AND THE CRYSTAL-STRUCTURE OF THE MODEL-COMPOUND [RH(COD)(HBZTU)CL] [J].

CAUZZI, D ;

LANFRANCHI, M ;

MARZOLINI, G ;

PREDIERI, G ;

TIRIPICCHIO, A ;

COSTA, M ;

ZANONI, R .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 488 (1-2) :115-125

[9] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION [J].

CHINCHILLA, R ;

NAJERA, C ;

SANCHEZAGULLO, P .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1393-1402

[10]

CONSIGLIO G, 1993, CATALYTIC ASYMMETRIC, P273

← 1 2 3 4 →