Unknown

Dataset Information

0

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of ?-, ?- and ?-lactones.

ABSTRACT: Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted ?-, ?-, and ?-lactones in good to excellent yields.

SUBMITTER: Christopher A 

PROVIDER: S-EPMC3845887 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Christopher Aaron A   Brandes Dahniel D   Kelly Stephen S   Minehan Thomas G TG  

Organic & biomolecular chemistry 20131010 44

Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields. ...[more]

Similar Datasets

Unknown Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers.
| S-EPMC2635117 | biostudies-literature
Unknown [3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.
| S-EPMC3087817 | biostudies-literature
Unknown Sequential Diels-Alder/[3,3]-sigmatropic rearrangement reactions of ?-nitrostyrene with 3-methyl-1,3-pentadiene.
| S-EPMC3817504 | biostudies-literature
Unknown A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles.
| S-EPMC2874392 | biostudies-literature
Unknown Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements.
| S-EPMC3778381 | biostudies-literature
Unknown Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.
| S-EPMC5870476 | biostudies-other
Unknown Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment.
| S-EPMC6201310 | biostudies-literature
Unknown A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.
| S-EPMC2504469 | biostudies-literature
Unknown Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers.
| S-EPMC3135071 | biostudies-literature
Unknown Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.
| S-EPMC4518476 | biostudies-literature