Pd-Catalyzed regio- and enantioselective allylic substitution with 2-pyridones

An efficient method for the asymmetric synthesis of N -substituted 2-pyridones via Pd-catalyzed regio- and enantioselective allylic substitution of hydroxyl-containing allylic carbonates with 2-pyridones has been developed. By using a palladium complex in situ generated from Pd 2 (dba) 3 ·CHCl 3 and...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 87; pp. 13168 - 13171
Main Authors Khan, Sardaraz, Shah, Babar Hussain, Khan, Ijaz, Li, Meiqi, Zhang, Yong Jian
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 29.10.2019
Royal Society of Chemistry
Subjects
Carbonates
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chloroform
Enantiomers
High performance liquid chromatography
NMR
Nuclear magnetic resonance
Palladium
Physical Sciences
Science & Technology
Substitutes
AMINATION
VINYL AZIRIDINES
VINYLETHYLENE CARBONATES
ALKYLATION
CONSTRUCTION
ASYMMETRIC DECARBOXYLATIVE CYCLOADDITION
CONVERTING ENZYME-INHIBITORS
BOND
TERTIARY
CONJUGATE ADDITION
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Summary:An efficient method for the asymmetric synthesis of N -substituted 2-pyridones via Pd-catalyzed regio- and enantioselective allylic substitution of hydroxyl-containing allylic carbonates with 2-pyridones has been developed. By using a palladium complex in situ generated from Pd 2 (dba) 3 ·CHCl 3 and phosphoramidite L2 as a ligand, the process allowed rapid access to N -substituted 2-pyridones with complete chemo- and regioselectivities and good to high enantioselectivities. An efficient method for the asymmetric synthesis of N -substituted 2-pyridones via a Pd-catalyzed regio- and enantioselective allylic substitution of hydroxyl-containing allylic carbonates with 2-pyridones has been developed.
Bibliography:1
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C NMR spectra of the products. See DOI
10.1039/c9cc07482a
Electronic supplementary information (ESI) available: Detailed experimental procedures; characterization data of all of the new compounds; copies of HPLC chromatographs, and
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SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc07482a