Synthesis of long-chain polyketide fragments by reaction of 1,3-dioxy-1,3-dienes with allylsilanes: Umpolung with sulfur dioxide
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 elimination of SO2, valuable polyketide precursors are obtained.
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Keywords: Bond-forming reaction ; diels-alder addition ; methyl sulfones ; stereoselective-synthesis ; polyfunctional sulfones ; 4-component ; synthesis ; aldol reaction ; one-pot ; desymmetrization ; acids
Swiss Fed Inst Technol, Inst Mol & Biol Chem, EPFL, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08