Dynamic Kinetic Asymmetric Domino Oxa-Michael/Carbocyclization by Combination of Transition-Metal and Amine Catalysis: Catalytic Enantioselective Synthesis of Dihydrofurans

Into the pot: A one‐pot highly chemo‐ and enantioselective catalytic domino oxa‐Michael/carbocyclization between α,β‐unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition‐metal and amine catalysis to afford functionalize...

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Published in:Chemistry : a European journal 2010-12, Vol.16 (47), p.13930-13934
Main Authors: Lin, Shuangzheng, Zhao, Gui-Ling, Deiana, Luca, Sun, Junliang, Zhang, Qiong, Leijonmarck, Hans, Córdova, Armando
Format: Article
Language:English
Subjects:
Amines - chemistry
asymmetric catalysis
Catalysis
Chemistry
co-catalysis
Crystallography, X-Ray
Cyclization
domino reactions
furans
Furans - chemical synthesis
Furans - chemistry
Kemi
Kinetics
Molecular Dynamics Simulation
Molecular Structure
NATURAL SCIENCES
NATURVETENSKAP
Organic chemistry
Organisk kemi
palladium
Palladium - chemistry
Stereoisomerism
Transition Elements - chemistry
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Summary:Into the pot: A one‐pot highly chemo‐ and enantioselective catalytic domino oxa‐Michael/carbocyclization between α,β‐unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition‐metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r.
ISSN:0947-6539
1521-3765
1521-3765
DOI:10.1002/chem.201001992