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April 8, 2026Synlett0 citations

DBU-Catalyzed Deconjugative Alkylations of 2-Alkylidene Indanones and Tetralones with Alkenes and Synthesis of Spirocyclic δ-Lactones

SBSaikumar BandaLJLasse JohannßenMBMalte Brasholz

Key Points

  • This research aims to explore DBU-catalyzed alkylation reactions to synthesize complex spirocyclic compounds.
  • Utilized DBU as a catalyst for α-alkylation of 2-butylidene indanones and tetralones with alkenes.
  • Conducted reactions under mild conditions to evaluate yield and selectivity.
  • Further converted alkylated products to unsaturated alkenoic acids for lactonization.
  • Achieved moderate to excellent yields of α,α-disubstituted β,γ-unsaturated indanones and tetralones.
  • Synthesized high yields of valuable spirocyclic δ-lactones through diastereoselective lactonization processes.

Abstract

1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) catalyzes the deconjugative α-alkylation of 2-butylidene 1-indanone and 1-tetralone with electrophilic alkenes, to give α,α-disubstituted β,γ-unsaturated indanone and tetralone products, under mild conditions, and in moderate to excellent yields. Further elaboration of the 1-indanone and 1-tetralone-derived skipped enones gave δ,ɛ-unsaturated alkenoic acids, which underwent diastereoselective iodo- and epoxylactonizations, furnishing valuable 4.5- and 5.5-spirocyclic δ-lactones in high yields.

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Cite This Study

Banda et al. (2026) studied this question.

synapsesocial.com/papers/69d5f17974eaea4b11a7afddhttps://doi.org/10.1055/a-2849-0894
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