Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)

Molecules. 2015 Sep 17;20(9):17041-57. doi: 10.3390/molecules200917041.

Abstract

Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product.

Keywords: dioxolane; dioxolanyl cation; hypervalent iodine; oxidation; stereoselective synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Dioxolanes / chemistry*
  • Iodine / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkenes
  • Dioxolanes
  • Iodine