Organocatalyzed Synthesis of Bicyclic γ-Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β-Keto Esters to Benzoyl Acrylonitriles

A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition of cyclic beta-keto esters to benzoyl acrylonitriles to afford the corresponding adducts. This was followed by the transformation of the nitrile group into an amide group, resulting in bicyclic gamm...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 13; no. 2
Main Authors Matsushima, Yasuyuki, Kubokawa, Satsuki, Watanabe, Mia, Nakashima, Kosuke, Hirashima, Shin-ichi, Miura, Tsuyoshi
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.02.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETOESTERS
ALDEHYDES
asymmetric conjugate addition
AMINO ALCOHOL ORGANOCATALYSTS
QUATERNARY
MICHAEL ADDITION
SKELETON
benzoyl acrylonitrile
bicyclic gamma-lactam
cyclic beta-keto ester
PYRROLIDINE-DIAMINOMETHYLENEMALONONITRILE ORGANOCATALYST
NITROOLEFINS
organocatalyst
NITROALKENES
CYCLIZATION
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Summary:A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition of cyclic beta-keto esters to benzoyl acrylonitriles to afford the corresponding adducts. This was followed by the transformation of the nitrile group into an amide group, resulting in bicyclic gamma-lactam derivatives in good yields with excellent enantioselectivities (up to 99 % ee). As far as we know, this is the first study to synthesize chiral bicyclic gamma-lactam derivatives from cyclic beta-keto esters and benzoyl acrylonitriles.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300620