Recent Advances in Iridium-Catalyzed Asymmetric Hydrogenation: New Catalysts, Substrates and Applications in Total Synthesis

被引:9
作者
Ganic, Adnan [1 ]
Rageot, Denise [1 ]
Troendlin, Lars [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
基金
瑞士国家科学基金会;
关键词
Asymmetric catalysis; Boron; Hydrogenation; Iridium; Natural products; P; O-Ligands; HIGHLY ENANTIOSELECTIVE HYDROGENATION; ABSOLUTE-CONFIGURATION; FORMAL SYNTHESIS; C=C BOND; OLEFINS; LIGANDS; ALPHA; CONSTRUCTION; COMPLEXES; VERSATILE;
D O I
10.2533/chimia.2012.187
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iridium-catalyzed asymmetric hydrogenation has emerged as a highly efficient method for the synthesis of enantiomerically pure compounds. This account summarizes our recent efforts in this field. We have developed a new type of P,O-ligand that was successfully applied to the asymmetric hydrogenation of alpha,beta-unsaturated carbonyl compounds. Furthermore we have demonstrated the potential of known iridium catalysts in the hydrogenation of alpha,beta-unsaturated boronic esters. And finally we could demonstrate the utility of iridium-catalyzed asymmetric hydrogenation in the formal synthesis of the natural product Platensimycin.
引用
收藏
页码:187 / 191
页数:5
相关论文
共 69 条
[1]  
[Anonymous], CHEMMEDCHEM, DOI DOI 10.1002/cmdc.200600145
[2]   Iridium-Catalyzed Asymmetric Hydrogenation of N-Protected Indoles [J].
Baeza, Alejandro ;
Pfaltz, Andreas .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (07) :2036-2039
[3]   Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Enamines [J].
Baeza, Alejandro ;
Pfaltz, Andreas .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (10) :2266-2269
[4]   Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins [J].
Bell, S ;
Wüstenberg, B ;
Kaiser, S ;
Menges, F ;
Netscher, T ;
Pfaltz, A .
SCIENCE, 2006, 311 (5761) :642-644
[5]   (+)- and (-)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity [J].
Bianco, Graziela G. ;
Ferraz, Helena M. C. ;
Cost, Arinice M. ;
Costa-Lotufo, Leticia V. ;
Pessoa, Claudia ;
de Moraes, Manoel O. ;
Schrems, Marcus G. ;
Pfaltz, Andreas ;
Silva, Luiz F., Jr. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2561-2566
[6]   DEVELOPMENT OF A SIMPLE GENERAL PROCEDURE FOR SYNTHESIS OF PURE ENANTIOMERS VIA CHIRAL ORGANOBORANES [J].
BROWN, HC ;
SINGARAM, B .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (08) :287-293
[7]   VERSATILE ALPHA-PINENE-BASED BORANE REAGENTS FOR ASYMMETRIC SYNTHESES [J].
BROWN, HC ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :1-19
[8]   THE BORON APPROACH TO ASYMMETRIC-SYNTHESIS [J].
BROWN, HC ;
RAMACHANDRAN, PV .
PURE AND APPLIED CHEMISTRY, 1991, 63 (03) :307-316
[9]   New P,N Ligands for asymmetric Ir-catalyzed reactions [J].
Bunlaksananusorn, T ;
Polborn, K ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3941-3943
[10]   Asymmetric hydrogenation of di and trisubstituted enol phosphinates with N,P-ligated iridium complexes [J].
Cheruku, Pradeep ;
Diesen, Jarle ;
Andersson, Pher G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (16) :5595-5599