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- Title
Controlling Cyclic Dienamine Reactivity in Radical tert‐Alkylation for Molecular Diversity to Synthesize Multicyclic Compounds Possessing a Quaternary Carbon.
- Authors
Kusano, Shinjiro; Nishikata, Takashi
- Abstract
Synthesis of diverse sterically congested molecules from a single important intermediate is one of the ideal synthetic strategies in organic synthesis. In this paper, we found that γ‐oxoalkyl substituted cyclohexenone derivatives (OAC) possessing a quaternary carbon are a useful key intermediate to derive both congested fused [5,6] rings and spirocycles. For this purpose, we have established an efficient synthetic method to obtain OAC by tertiary alkylation of β‐methylcyclohexenone derivatives using α‐bromocarbonyl compounds as a tertiary alkyl source. The key to the success of this reaction is controlling the reactivity of the dienamine intermediate. While there have been many reports on enamine reactions, dienamine reactions have not been well studied. Herein, we report controlling reactivity of dienamines and molecular diversification from OAC.
- Subjects
RADICALS (Chemistry); ORGANIC synthesis; ALKYL compounds; CARBON; ALKYLATION; ENAMINES
- Publication
Chemistry - A European Journal, 2024, Vol 30, Issue 17, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202304215