Organocatalytic Enantioselective Tandem Michael Addition and Cyclization Reaction of Trisubstituted 2‐Nitro‐1,3‐enynes with Cyclic 1,3‐Diketones

An enantioselective tandem Michael addition/cyclization reaction between trisubstituted 2‐nitro‐1,3‐enynes and cyclic 1,3‐diketones catalyzed by a chiral organosquaramide catalyst in the presence of Ag2CO3 was developed. The chiral functionalized chromene products could be obtained in good yield and...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-06, Vol.359 (11), p.1892-1900
Main Authors: Xing, Zi‐Min, Song, Le‐Le, Li, Feng‐Xing, Xu, Nian‐Sheng, Wang, Lu‐Feng, Shi, Zi‐Fa, Cao, Xiao‐Ping
Format: Article
Language:English
Subjects:
Catalysts
chromenes
Crystallography
cyclization
Diketones
enynes
Michael addition
organocatalysis
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Summary:An enantioselective tandem Michael addition/cyclization reaction between trisubstituted 2‐nitro‐1,3‐enynes and cyclic 1,3‐diketones catalyzed by a chiral organosquaramide catalyst in the presence of Ag2CO3 was developed. The chiral functionalized chromene products could be obtained in good yield and in 80–99% enantiomeric excess. The structures and absolute configurations of some of the products were confirmed by X‐ray crystallographic analysis.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700085