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.


Published in:
Journal of Organic Chemistry, 69, 12, 4272-4275
Year:
2004
ISSN:
0022-3263
Keywords:
Note:
Ecole Polytech Fed Lausanne, BCH, Swiss Fed Inst Technol, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland.
Other identifiers:
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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