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Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: asymmetric synthesis of polypropionate fragments


, : Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: asymmetric synthesis of polypropionate fragments. Journal of Organic Chemistry 69(12): 4272-4275

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)/PPh(3) 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.

US$19.90

PMID: 15176859

DOI: 10.1021/jo0357622


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