Palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary carbon stereocenter

A palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary stereocenter at the 3-position has been achieved by the reaction of gamma-methylidene-delta-valerolactones with alkyl isocyanates. High enantioselectivity has been realized by employing a newly synthesized chiral phosph...

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Published inChemical communications (Cambridge, England) Vol. 48; no. 79; pp. 9936 - 9938
Main Authors Shintani, Ryo, Ito, Tomoaki, Nagamoto, Midori, Otomo, Haruka, Hayashi, Tamio
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.10.2012
Subjects
Carbon - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Isocyanates - chemistry
Lactones - chemistry
Ligands
Molecular Conformation
Organophosphorus Compounds - chemistry
Palladium - chemistry
Physical Sciences
Pyrrolidinones - chemistry
Science & Technology
Stereoisomerism
KETENE SILYL ACETAL
ALPHA CONVERTING-ENZYME
GAMMA-LACTAM
(PI-ALLYL)PALLADIUM COMPLEXES
SELECTIVE INHIBITORS
STEREOSELECTIVE-SYNTHESIS
NUCLEOPHILIC-ATTACK
PHOSPHORAMIDITE LIGAND
ENANTIOSELECTIVE CONSTRUCTION
CONJUGATE ADDITION
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Summary:A palladium-catalyzed asymmetric synthesis of 2-pyrrolidinones with a quaternary stereocenter at the 3-position has been achieved by the reaction of gamma-methylidene-delta-valerolactones with alkyl isocyanates. High enantioselectivity has been realized by employing a newly synthesized chiral phosphoramidite ligand.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc35259a