AI Article Synopsis
- - The trimerization reaction of bromovinylsulfone 1 led to the formation of cyclohexene 6 as the only diastereoisomer.
- - The optimized method produced cyclohexene 6 with a yield of 49%.
- - The proposed mechanism for this reaction involves a series of steps including S2' additions, [3,3]-rearrangements, and a final stereoselective intramolecular conjugate addition, supported by computational calculations.
Article Abstract
A unprecedented base-induced trimerization of bromovinylsulfone 1 afforded the cyclohexene 6 as a single diastereoisomer. Optimization of this reaction gave the adduct 6 in 49% yield. A mechanistic rationale for the trimerization involving consecutive S2' additions and [3,3]-rearrangements and a final stereoselective intramolecular conjugate addition is proposed and supported by M06-2X density functional theory calculations.
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| http://dx.doi.org/10.1039/c7ob01121k | DOI Listing |
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