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Bi(OAc)3/Chiral Phosphoric Acid-Catalyzed Enantioselective 1,2- and Formal 1,4-Allylation Reaction of β,γ-Unsaturated α-Ketoesters

Xiang-Shuai Liu, Yao Li and Xin Li*

*State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China, Email:

X.-S. Liu, Y. Li, X. Li, Org. Lett., 2021, 23, 9128-9133.

DOI: 10.1021/acs.orglett.1c03453

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The combination of Bi(OAc)3 and a chiral phosphoric acid catalyzes a highly efficient asymmetric 1,2-allylation reaction of β,γ-unsaturated α-ketoesters under mild conditions. A subsequent anionic oxy-Cope rearrangement achieves an asymmetric formal 1,4-allylation reaction in a one-pot process.

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DFT-calculated transition states of 1,2-allylation reactions

Key Words

homoallylic alcohols

ID: J54-Y2021