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

A highly efficient asymmetric 1,2-allylation reaction of β,γ-unsaturated α-ketoesters was realized by using a Bi(OAc)3/chiral phosphoric acid catalyst system under mild conditions. Meanwhile, using this combined strategy of enantioselective 1,2-allylation and subsequent anionic oxy-Cope rearrangement, the asymmetric formal 1,4-allylation reaction was achieved by a one-pot process. These reactions offer rapid access to an array of homoallylic tertiary alcohols and γ-allyl-α-ketoesters with good yields and excellent enantioselectivities. Density functional theory calculations were conducted to interpret the high enantioselectivity.

• Publication year

  2021

• Venue

  Organic Letters

• Publication date

  2021-11-15

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.1c03453PMID 34779206
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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