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- Title
Nucleophile Coordination Enabled Regioselectivity in Palladium‐Catalyzed Asymmetric Allylic C−H Alkylation.
- Authors
Fan, Lian‐Feng; Luo, Shi‐Wei; Chen, Shu‐Sen; Wang, Tian‐Ci; Wang, Pu‐Sheng; Gong, Liu‐Zhu
- Abstract
Branched selectivity in asymmetric allylic C−H alkylation is enabled by using 2‐acylimidazoles as nucleophiles in the presence of a chiral phosphoramidite‐palladium catalyst. A wide range of terminal alkenes, including 1,4‐dienes and allylarenes, are nicely tolerated and provide chiral 2‐acylimidazoles in moderate to high yields and with high levels of regio‐, and enantio‐, and E/Z‐selectivities. Mechanistic studies using density‐functional theory calculations suggest a nucleophile‐coordination‐enabled inner‐sphere attack mode for the enantioselective carbon–carbon bond‐forming event.
- Subjects
ALLYLIC alkylation; ALLYLIC amination; ALKENES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 47, p16962
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201908960