Development of a new carbon-carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones

V Narkevitch, S Megevand, K Schenk…

Index: Narkevitch; Megevand; Schenk; Vogel Journal of Organic Chemistry, 2001 , vol. 66, # 15 p. 5080 - 5093

Full Text: HTML

Citation Number: 34

Abstract

At low temperature 1-alkoxy-1, 3-dienes add to sulfur dioxide activated by a Lewis or Brønstedt 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 ...

Related Articles:

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 …

[Megevand, Sophie; Moore, Jonathan; Schenk, Kurt; Vogel, Pierre Tetrahedron Letters, 2001 , vol. 42, # 4 p. 673 - 675]

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 …

[Megevand, Sophie; Moore, Jonathan; Schenk, Kurt; Vogel, Pierre Tetrahedron Letters, 2001 , vol. 42, # 4 p. 673 - 675]

More Articles...