Journal article

New carbon-carbon bond formation through oxyallylation of enoxysilanes with sulfur dioxide adduct of 1-methoxybutadiene. Stereoselective synthesis of (Z)-4-methoxy-6-oxoalk-2-enyl methyl sulfones

Mixtures of 1-methoxybutadiene, trimethylsilyl enol ethers, SO2 and a Lewis acid catalyst generate trimethylsilyl (Z)-4-methoxy-6-oxoalk-2-enesulfinates that can be converted into 4-methoxy-6-oxoalk-2-enyl methyl sulfones and 5-alkyl-4-methoxy-6-oxoalk-2-enyl methyl sulfones with 100% (Z) selectivity and good syn diastereoselectivity for the 5-alkyl and 4-methoxy substituents. (C) 1997 Elsevier Science Ltd.


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