358725-08-3Relevant academic research and scientific papers
Synthesis of long-chain polyketide fragments by reaction of 1,3-dioxy-1,3-dienes with allylsilanes: Umpolung with sulfur dioxide
Turks, Maris,Fonquerne, Freddy,Vogel, Pierre
, p. 1053 - 1056 (2007/10/03)
(Equation presented) In the presence of a Lewis or protic acid and at low temperature, 1,3-dioxy-1,3-dienes add to sulfur dioxide generating zwitterionic intermediates that can react with carbon nucleophiles such as allylsilanes. After a retro-ene elimina
Development of a new carbon - carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones
Narkevitch,Megevand,Schenk,Vogel
, p. 5080 - 5093 (2007/10/03)
At low temperature 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or Bronstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting β,γ-unsaturated silyl sulfinates can be desilylated and reacted with methyl iodide to provide polyfunctional sulfones. Exploratory studies of this four-component synthesis of sulfones are reported. Enantiomerically pure derivatives containing up to three new stereogenic centers can be obtained using enantiomerically pure (E,E)-1 -alkoxy-2-methylpenta-1,3-dienes derived from α-methyl benzyl alcohols, including the Greene's chiral auxiliary. The stereochemistry of the reactions is consistent with a mechanism involving the suprafacial hetero-Diels - Alder addition of sulfur dioxide to the 1-alkoxy-1,3-dienes that are rapidly ionized into zwitterionic intermediates.
