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- Title
Catalytic Decarboxylative Asymmetric Allylic Alkylation for the Synthesis of Axially Chiral Biaryls.
- Authors
Cho, Hyun‐A; Kim, Sangji; Hwang, Minyoung; Dongbang, Sun; Kwon, Yongseok
- Abstract
Herein, we report a palladium‐catalyzed atroposelective decarboxylative asymmetric allylic alkylation. A chiral palladium complex with a phosphoramidite ligand effectively desymmetrizes biaryls containing cinnamyl carbonate with excellent enantioselectivities. The addition of a catalytic amount of base accelerates the reaction process without loss of enantioselectivity. Cross‐over experiment provides mechanistic insight, suggesting that allyl palladium complex primarily dissociates from the original biaryl substrate and deliver allyl species intermolecularly. Analysis of product distribution at various time points indicates that secondary kinetic resolution plays a crucial role in achieving remarkable atroposelectivity.
- Subjects
ALLYLIC alkylation; PALLADIUM compounds; ALKYLATION; KINETIC resolution
- Publication
Asian Journal of Organic Chemistry, 2024, Vol 13, Issue 3, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300606