Highly efficient asymmetric hydrogenation of alkyl aryl ketones catalyzed by iridium complexes with chiral planar ferrocenyl phosphino-thioether ligands

被引：54
作者：
Le Roux, Erwan
Malacea, Raluca
Manoury, Eric
Poli, Rinaldo
Gonsalvi, Luca
Peruzzini, Maurizio
机构：
[1] CNR, ICCOM, I-50019 Sesto Fiorentino, Firenze, Italy
[2] CNRS, LCC, F-31077 Toulouse 4, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 03期
关键词：
alkyl aryl ketones; asymmetric catalysis; ferrocene ligands; hydrogenation; iridium; P; S ligands;
D O I：
10.1002/adsc.200600350
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Iridium complexes of planar-chiral ferrocenyl phosphine-thioether ligands were tested in the hydrogenation of simple ketones. Optimization of the conditions led to a highly active catalytic system with turnover numbers up to 915 and turnover frequencies up to ca. 250 h(-1). Furthermore, very high enantioselectivities (up to > 99 %) together with complete conversions were obtained for the asymmetric hydrogenation of various acetophenones at 10 degrees C.
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页码：309 / 313
页数：5
相关论文
共 47 条
[1]   CATALYTIC AND STRUCTURAL STUDIES OF RHI COMPLEXES OF (-)-(2S,4S)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE - ASYMMETRIC HYDROGENATION OF ACETOPHENONEBENZYLIMINE AND ACETOPHENONE [J].
BAKOS, J ;
TOTH, I ;
HEIL, B ;
SZALONTAI, G ;
PARKANYI, L ;
FULOP, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :263-276
[2]   Kinetic aspects of nonlinear effects in asymmetric catalysis [J].
Blackmond, DG .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :402-411
[3]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[4]   A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones [J].
Burk, MJ ;
Hems, W ;
Herzberg, D ;
Malan, C ;
Zanotti-Gerosa, A .
ORGANIC LETTERS, 2000, 2 (26) :4173-4176
[5]   Ruthenium-catalysed asymmetric hydrogenation of ketones using QUINAPHOS as the ligand [J].
Burk, S ;
Franciò, G ;
Leitner, W .
CHEMICAL COMMUNICATIONS, 2005, (27) :3460-3462
[6]   Recent developments in catalytic asymmetric hydrogenation employing P-chirogenic diphosphine ligands [J].
Crépy, KVL ;
Imamoto, T .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :79-101
[7]   Iridium complexes with chiral and achiral β-aminophosphane ligands:: Catalysts for >C=O hydrogenation and H/D exchange involving both homo- and heterolytic H2 activation [J].
Dahlenburg, L ;
Götz, R .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (04) :888-905
[8]  
Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
[9]  
2-9
[10]  
Fehring V, 1998, ANGEW CHEM INT EDIT, V37, P1827, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1827::AID-ANIE1827>3.0.CO
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