Highly enantioselective [4+2] cyclization of chloroaldehydes and 1-azadienes catalyzed by N-heterocyclic carbenes

Highly functionalized dihydropyridinones were synthesized via the N-heterocyclic carbene-catalyzed enantioselective [4 + 2] annulation of alpha-chloroaldehydes and azadienes. Hydrogenation of the resulted dihydropyridinones afforded the corresponding piperidinones with high enantiopurity.

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 48; no. 88; pp. 10907 - 10909
Main Authors Jian, Teng-Yue, Sun, Li-Hui, Ye, Song
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2012
Subjects
Aldehydes - chemistry
Aza Compounds - chemistry
Carbenes
Chemistry
Chemistry, Multidisciplinary
Cyclization
Hydrogenation
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Physical Sciences
Pyridones - chemistry
Science & Technology
Stereoisomerism
NUCLEOPHILIC CARBENES
ROOM-TEMPERATURE
CYCLOADDITION
DIELS-ALDER REACTIONS
ALPHA,BETA-UNSATURATED ALDEHYDES
ENOLATE EQUIVALENTS
STEREOSELECTIVE-SYNTHESIS
GAMMA-BUTYROLACTONES
4-PI PARTICIPATION
BETA-LACTAMS
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Summary:Highly functionalized dihydropyridinones were synthesized via the N-heterocyclic carbene-catalyzed enantioselective [4 + 2] annulation of alpha-chloroaldehydes and azadienes. Hydrogenation of the resulted dihydropyridinones afforded the corresponding piperidinones with high enantiopurity.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc35273g