A novel chiral aliphatic-aromatic diamine promoted direct, highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins under solvent-free conditions

A series of new highly efficient chiral aliphatic–aromatic diamine catalysts have been designed and successfully applied to the asymmetric Michael addition of cyclohexanone with nitroolefins under solvent‐free conditions without any acidic additives. The desired adducts were obtained in high yields...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2010-10, Vol.22 (9), p.855-862
Main Authors: Miao, Shifeng, Bai, Jinjin, Yang, Jin, Zhang, Yawen
Format: Article
Language:English
Subjects:
Additives
Adducts
aliphatic-aromatic diamine
asymmetric
Asymmetry
Catalysis
Catalysts
Chirality
Cyclohexanone
Diamines
Michael addition
Michael reaction
nitroolefin
Reproduction
solvent free
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Summary:A series of new highly efficient chiral aliphatic–aromatic diamine catalysts have been designed and successfully applied to the asymmetric Michael addition of cyclohexanone with nitroolefins under solvent‐free conditions without any acidic additives. The desired adducts were obtained in high yields with excellent enantio‐ and diastereoselectivities of syn products (up to >99% ee, >99:1 dr). Chirality 2010. © 2010 Wiley‐Liss, Inc
ISSN:0899-0042
1520-636X
1520-636X
DOI:10.1002/chir.20847