Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: Asymmetric synthesis of polypropionate fragments
At low temperature, 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or protic acid generating zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma-unsaturated silyl sulfinates can be desilylated by 1:1 Pd(OAc)(2)/PPh3 catalyst, liberating the corresponding beta,gamma-unsaturated sulfinic acids that undergo smooth and highly stereoselective retro-ene eliminations of sulfur dioxide. The method has been applied to generate enantiomerically pure polypropionate fragments.
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Ecole Polytech Fed Lausanne, BCH, Swiss Fed Inst Technol, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08