Synthesis of (E)-1-Aryl-2-methyl-3-alkyl-2-propen-1-ones via Allylic Sulfoxide-Sulfenate Ester Rearrangements

Article abstract of DOI:10.1021/jo00344a013

A synthon for vinyl anion 2 has been designed as the cornerstone for a versatile synthesis of (E)-1-aryl-2-methyl-3-alkyl-2-propen-1-ones (1).The choice of the allylic sulfoxide-sulfenate ester rearrangement as a synthesis conduit leads to formation of the desired E isomers stereoselectively.Attempted tetrahydropyran ring opening of enone 7c was not successful.