Highly Asymmetric Michael Addition to α,β-Unsaturated Ketones Catalyzed by 9-Amino-9-deoxyepiquinine

Michael–Michael–retro‐Michael cascade reactions are promoted by the highly efficient organocatalyst 9‐amino‐9‐deoxyepiquinine (1). The asymmetric direct vinylogous Michael addition of α,α‐dicyanoalkenes to α,β‐unsaturated ketones may be followed by an intramolecular Michael addition and a retro‐Mich...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-01, Vol.46 (3), p.389-392
Main Authors: Xie, Jian-Wu, Chen, Wei, Li, Rui, Zeng, Mi, Du, Wei, Yue, Lei, Chen, Ying-Chun, Wu, Yong, Zhu, Jin, Deng, Jin-Gen
Format: Article
Language:English
Subjects:
amines
Amines - chemistry
asymmetric synthesis
Butanones - chemistry
Catalysis
domino reactions
Ketones - chemistry
Michael addition
Molecular Structure
organocatalysis
Quinolizines - chemistry
Stereoisomerism
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Summary:Michael–Michael–retro‐Michael cascade reactions are promoted by the highly efficient organocatalyst 9‐amino‐9‐deoxyepiquinine (1). The asymmetric direct vinylogous Michael addition of α,α‐dicyanoalkenes to α,β‐unsaturated ketones may be followed by an intramolecular Michael addition and a retro‐Michael reaction to afford polysubstituted 2‐cyclohexen‐1‐one derivatives with high enantioselectivity (see example).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603612