Chiral N-heterocyclic carbene/Lewis acid cooperative catalysis of the reaction of 2-aroylvinylcinnamaldehydes: a switch of the reaction pathway by Lewis acid activation

The chiral N-heterocyclic carbene/Lewis acid co-catalyzed reaction of 2-aroylvinylcinnamaldehydes produced good yields of indeno-[1,2-c]furan-1-one derivatives with excellent enantioselectivity and diastereoselectivity. A switch of intramolecular cyclization to intermolecular dimerization was achiev...

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Published inChemical communications (Cambridge, England) Vol. 52; no. 4; pp. 788 - 791
Main Authors Wang, Zhan-Yong, Ding, Ya-Li, Wang, Gang, Cheng, Ying
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Activation
Carbenes
Catalysis
Chemistry
Chemistry, Multidisciplinary
Derivatives
Lewis acid
Pathways
Physical Sciences
Science & Technology
Switches
Triazoles
ANNULATIONS
ASYMMETRIC-SYNTHESIS
STRATEGY
CONSTRUCTION
SELECTIVE SYNTHESIS
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
UMPOLUNG
ENALS
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Summary:The chiral N-heterocyclic carbene/Lewis acid co-catalyzed reaction of 2-aroylvinylcinnamaldehydes produced good yields of indeno-[1,2-c]furan-1-one derivatives with excellent enantioselectivity and diastereoselectivity. A switch of intramolecular cyclization to intermolecular dimerization was achieved by the cooperative catalysis of chiral triazole carbene and Ti(OPr-i)(4) catalysts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08866f