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- Title
Organocatalyzed Synthesis of Bicyclic γ‐Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β‐Keto Esters to Benzoyl Acrylonitriles.
- Authors
Matsushima, Yasuyuki; Kubokawa, Satsuki; Watanabe, Mia; Nakashima, Kosuke; Hirashima, Shin‐ichi; Miura, Tsuyoshi
- Abstract
A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition of cyclic β‐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 γ‐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 γ‐lactam derivatives from cyclic β‐keto esters and benzoyl acrylonitriles.
- Subjects
ACRYLONITRILE; ESTERS; AMIDES; LACTAMS; TRANSFORMATION groups; NITROALKENES
- Publication
Asian Journal of Organic Chemistry, 2024, Vol 13, Issue 2, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300620