What question did this study set out to answer?

This research aims to explore DBU-catalyzed alkylation reactions to synthesize complex spirocyclic compounds.

April 8, 2026

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

SBSaikumar BandaUniversity of Rostock LJLasse JohannßenUniversity of Rostock MBMalte BrasholzUniversity of Rostock

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.

Demander à l'IA

Bookmark

View Full Paper