334813-02-4Relevant academic research and scientific papers
Four component synthesis of (Z)-4-alkoxy-1,3-dimethylalk-2-enyl methyl sulfones: On the intermediacy of sultines (3,6-dihydro-1,2-oxathiin-2-oxides) arising from suprafacial hetero-Diels-Alder additions of sulfur dioxide
Megevand, Sophie,Moore, Jonathan,Schenk, Kurt,Vogel, Pierre
, p. 673 - 675 (2001)
The reactions of (E,E)-1-benzyloxy-2-methylpenta-1,3-diene (9) with 3,3-dimethyl-2-(trimethylsilyloxy)butene and (Z)-3-(trimethylsilyloxy)pent-2-ene in SO2 and a Lewis acid give silyl sulfinates that are quenched with MeI to generate the corres
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.
