Phosphine-Catalyzed (3 + 2)/(3 + 2) Sequential Annulation of γ-Vinyl Allenoates: Access to Fused Carbocycles.

The first (3 + 2)/(3 + 2) sequential annulation of γ-vinyl allenoates with alkylidenemalononitriles enabled by phosphine catalysis has been reported. A broad range of structurally dense tetra- and penta-substituted bicyclic[3,3,0]octene derivatives, containing a quaternary center and three sequential stereogenic center, were synthesized in good to excellent yields. In this approach, three new C-C bonds are formed in one pot, and εC and αC of γ-vinyl allenoate are two electrophilic centers, whereas its γC exhibits nucleophilic reactivity.

• Publication year

  2019

• Venue

  Organic Letters

• Publication date

  2019-12-24

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.9b04176PMID 31873035
• 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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