Enantioselective addition of anthrones to α,β-unsaturated aldehydes

被引:26
作者
Alba, Andrea-Nekane [1 ]
Bravo, Natalia [1 ]
Moyano, Albert [1 ]
Rios, Ramon [1 ]
机构
[1] Univ Barcelona, Dept Quim Organ, Fac Quim, E-08028 Barcelona, Catalonia, Spain
关键词
ONE-POT; CATALYZED REACTIONS; ASYMMETRIC ENTRY; EPOXIDATION; ALKYLATION;
D O I
10.1016/j.tetlet.2009.04.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first examples of enantioselective addition of anthrones to of alpha,beta-unsaturated aldehydes are disclosed. The reaction was performed at -40 degrees C achieving high yields and enantioselectivities. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3067 / 3069
页数:3
相关论文
共 27 条
[1]   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
[2]  
Baik WP, 2004, B KOR CHEM SOC, V25, P491
[3]   Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes [J].
Balaguer, Andrea-Nekane ;
Companyo, Xavier ;
Calvet, Teresa ;
Font-Bardia, Merce ;
Moyano, Albert ;
Rios, Ramon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (02) :199-203
[4]   Control of four stereocentres in a triple cascade organocatalytic reaction [J].
Enders, Dieter ;
Hüettl, Matthias R. M. ;
Grondal, Christoph ;
Raabe, Gerhard .
NATURE, 2006, 441 (7095) :861-863
[5]   Iminium catalysis [J].
Erkkila, Anniina ;
Majander, Inkeri ;
Pihko, Petri M. .
CHEMICAL REVIEWS, 2007, 107 (12) :5416-5470
[6]   Highly enantio- and diastereoselective organocatalytic asymmetric domino Michael-Aldol reaction of β-ketoesters and α,β-unsaturated ketones [J].
Halland, N ;
Aburel, PS ;
Jorgensen, KA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1272-1277
[7]   Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis [J].
Ibrahem, I ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1952-1956
[8]   BASE-CATALYZED REACTIONS OF ANTHRONES WITH DIENOPHILES [J].
KOERNER, M ;
RICKBORN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2662-2672
[9]   ANTHRONES AS REACTIVE DIENES IN DIELS-ALDER REACTIONS [J].
KOERNER, M ;
RICKBORN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :6-9
[10]   ANTRACENEDIOLS AS REACTIVE DIENES IN BASE-CATALYZED CYCLOADDITIONS - REDUCTION CYCLOADDITION REACTIONS OF ANTHRAQUINONES [J].
KOERNER, M ;
RICKBORN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1373-1381