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- W2810130690 abstract "A new process of inverted formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes (DACs) to allylic systems to give polyfunctionalized cyclopentanes has been developed. Unlike the classical version of formal [3 + 2]-cycloaddition, a DAC acts in this process as a two-carbon synthon (1,2-zwitterionic reactivity type), while an alkene acts as a three-carbon synthon. Tetramethylethylene, allylbenzenes, homoallylbenzene, terminal and internal aliphatic alkenes, and methylenecyclobutane were successfully used as alkenes. Furthermore, in order to suppress annulation at the aromatic ring in 2-arylcyclopropane-1,1-dicarboxylates and enhance the selectivity of the reaction with the allylic system of alkenes, we suggested a new approach for managing the reactivity of DACs involving substitution at both ortho positions of the aromatic ring. Multinuclear NMR spectroscopy was used to study the structure of the 1,2-zwitterionic gallium complexes generated and their properties and to examine the mechanisms of the occurring reactions." @default.
- W2810130690 created "2018-07-10" @default.
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- W2810130690 date "2018-07-02" @default.
- W2810130690 modified "2023-10-18" @default.
- W2810130690 title "GaCl<sub>3</sub>-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems" @default.
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- W2810130690 doi "https://doi.org/10.1021/acs.joc.8b00959" @default.
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