Iridium-Catalyzed Asymmetric Hydrogenation of α-Alkylidene Succinimides

被引:103
作者
Liu, Yuanyuan [1 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; hydrogenation; iridium; ligand effects; synthetic methods; HIGHLY ENANTIOSELECTIVE HYDROGENATION; SPIRO AMINOPHOSPHINE LIGANDS; DIELS-ALDER REACTIONS; OXAZOLINE LIGANDS; 1,3-DIPOLAR CYCLOADDITIONS; ALLYLIC ALKYLATION; CARBONYL-COMPOUNDS; C(SP(3))-H BONDS; CHIRAL SWITCH; COMPLEXES;
D O I
10.1002/anie.201209126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not to be out PhOXed! The title reaction provides a new approach to chiral succinimide derivatives with excellent yields and ee values by using a low catalyst loading (0.05 mol %) and mild reaction conditions. Chiral 3-benzyl pyrrolidines and 1-hydroxypyrrolidine-2,5-diones, important structural motifs in natural products and pharmaceuticals, could be readily prepared. BARF -=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2203 / 2206
页数:4
相关论文
共 104 条
[1]  
[Anonymous], 2011, ANGEW CHEM
[2]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[3]  
[Anonymous], 2012, ANGEW CHEM, V124, P960
[4]  
[Anonymous], 2012, ANGEW CHEM
[5]   Structure activity studies of ring E analogues of methyllycaconitine.: Part 2:: Synthesis of antagonists to the α3β4*nicotinic acetylcholine receptors through modifications to the ester [J].
Bergmeier, SC ;
Ismail, KA ;
Arason, KM ;
McKay, S ;
Bryant, DL ;
McKay, DB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3739-3742
[6]   Use of an Iridium-Catalyzed Redox-Neutral Alcohol-Amine Coupling on Kilogram Scale for the Synthesis of a GlyT1 Inhibitor [J].
Berliner, Martin A. ;
Dubant, Stephane P. A. ;
Makowski, Teresa ;
Ng, Karl ;
Sitter, Barbara ;
Wager, Carrie ;
Zhang, Yinsheng .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (05) :1052-1062
[7]  
Blaser HU, 1999, CHIMIA, V53, P275
[8]  
Blaser HU, 2002, ADV SYNTH CATAL, V344, P17, DOI 10.1002/1615-4169(200201)344:1<17::AID-ADSC17>3.0.CO
[9]  
2-8
[10]   New mechanistic insights into the iridium- phosphanooxazoline-catalyzed hydrogenation of unfunctionalized olefins: A DFT and kinetic study [J].
Brandt, P ;
Hedberg, C ;
Andersson, PG .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :339-347