A Palladium/Chiral Amine Co-catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter

Polysubstituted 5‐ and 6‐membered carbocycles were synthesized by the title reaction. The one‐pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and c...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-06, Vol.52 (23), p.6050-6054
Main Authors: Ma, Guangning, Afewerki, Samson, Deiana, Luca, Palo-Nieto, Carlos, Liu, Leifeng, Sun, Junliang, Ibrahem, Ismail, Córdova, Armando
Format: Article
Language:English
Subjects:
Aldehydes
Amines
Amines - chemistry
asymmetric catalysis
carbocycles
Carbon
Cascades
Catalysis
co-catalysis
Cyclization
Dynamics
Hydrocarbons, Cyclic - chemical synthesis
Hydrocarbons, Cyclic - chemistry
Molecular Structure
Palladium
Palladium - chemistry
Protein Structure, Quaternary
quaternary carbon stereocenters
Relay
Stereoisomerism
Synthesis
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Summary:Polysubstituted 5‐ and 6‐membered carbocycles were synthesized by the title reaction. The one‐pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and chiral amine co‐catalysts.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201300559