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A new synthetic route to β-bromoprop-2-ynyl mixed acetals and bromovinyl bis-allyl mixed acetals, precursors of α-methylene-γ-butyrolactones
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1988
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β-Bromoprop-2-ynyl Mixed AcetalsEngineeringAllyl Allenyl Ethersβ-Bromoallenyl EthersBis-allyl Mixed AcetalsNew Synthetic RouteOrganic ChemistryCatalysisSynthetic ChemistryChemistryStereoselective SynthesisHalogenationAsymmetric CatalysisHomolytic CarbocyclizationEnantioselective Synthesis
Cohalogenation by N-bromosuccinimide in methanol of β-bromoallenyl ethers (3a–g) or allyl allenyl ethers (8d–f) affords unsaturated halogeno-compounds (5a–g) or (9d–f) which are converted via homolytic carbocyclization into α-methylene-γ-butyrolactones (7a–g).