Jump to main content
Jump to site search

Issue 26, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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., 2017,15, 5529-5534
  •   Request permissions

    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, 15, 5529
    DOI: 10.1039/C7OB01121K

Search articles by author

Spotlight

Advertisements