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An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone

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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 SN2′ additions and [3,3]-rearrangements and a final stereoselective intramolecular conjugate addition is proposed and supported by M06-2X density functional theory calculations.

Graphical abstract: An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone

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Publication details

The article was received on 08 May 2017, accepted on 08 Jun 2017 and first published on 09 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01121K
Citation: Org. Biomol. Chem., 2017, Advance Article
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    An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone

    B. Fisher, R. J. Lepage, J. M. White, Y. Ye, E. H. Krenske and M. A. Rizzacasa, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01121K

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