An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols

被引:137
作者
Quintard, Adrien [1 ]
Constantieux, Thierry [1 ]
Rodriguez, Jean [1 ]
机构
[1] Aix Marseille Univ, Cent Marseille, CNRS, ISm2,UMR 7313, F-13397 Marseille, France
关键词
asymmetric catalysis; dual catalysis; hydrogen transfer; iron; organocatalysis; MEDIATED 2+2+1 CYCLOADDITIONS; OPPENAUER-TYPE OXIDATION; METAL-DIENE COMPLEXES; C BOND FORMATION; TRANSITION-METAL; IRON-CATALYST; ALPHA; BETA-UNSATURATED ALDEHYDES; BORROWING HYDROGEN; ORGANIC-SYNTHESIS; CARBON-MONOXIDE;
D O I
10.1002/anie.201307295
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition reaction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12883 / 12887
页数:5
相关论文
共 65 条
[1]   Domino hydroformylation/enantioselective cross-aldol addition [J].
Abillard, Olivier ;
Breit, Bernhard .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1891-1895
[2]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[3]   Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].
Allen, Anna E. ;
MacMillan, David W. C. .
CHEMICAL SCIENCE, 2012, 3 (03) :633-658
[4]  
[Anonymous], 1999, Angew. Chem
[5]  
[Anonymous], 2006, ANGEW CHEM
[6]   The Catalytic Amination of Alcohols [J].
Baehn, Sebastian ;
Imm, Sebastian ;
Neubert, Lorenz ;
Zhang, Min ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2011, 3 (12) :1853-1864
[7]   A Highly Active Bifunctional Iridium Complex with an Alcohol/Alkoxide-Tethered N-Heterocyclic Carbene for Alkylation of Amines with Alcohols [J].
Bartoszewicz, Agnieszka ;
Marcos, Rocio ;
Sahoo, Suman ;
Inge, A. Ken ;
Zou, Xiaodong ;
Martin-Matute, Belen .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (45) :14510-14519
[8]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[9]  
Black PJ, 2001, ANGEW CHEM INT EDIT, V40, P4475, DOI 10.1002/1521-3773(20011203)40:23<4475::AID-ANIE4475>3.0.CO
[10]  
2-P