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.


Published in:
Tetrahedron Letters, 38, 35, 6197-6200
Year:
1997
ISSN:
0040-4039
Keywords:
Note:
Univ lausanne,chim sect,bch,ch-1015 lausanne,switzerland.
Laboratories:




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


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