American Chemical Society
ol8b01697_si_001.pdf (8.91 MB)

Enantioselective Synthesis of 5‑Alkylated Thiazolidinones via Palladium-Catalyzed Asymmetric Allylic C–H Alkylations of 1,4-Pentadienes with 5H‑Thiazol-4-ones

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journal contribution
posted on 2018-08-06, 13:36 authored by Tian-Ci Wang, Zhi-Yong Han, Pu-Sheng Wang, Hua-Chen Lin, Shi-Wei Luo, Liu-Zhu Gong
A palladium-catalyzed, enantioselective allylic C–H alkylation of 1,4-pentadienes with 5H-thiazol-4-ones has been developed. Under the cooperative catalysis of a palladium complex of chiral phosphoramidite ligand and an achiral Brønsted acid, a broad range of substituted 5H-thiazol-4-ones bearing sulfur-containing tertiary chiral centers were accessed from the allylic C–H alkylation in high levels of yields and enantioselectivities. Alkyl and aryl 1,4-pentadienes led to linear and branched allylation products, respectively.