Synthesis of Alkyl-Ynol-Ethers by Anti-Michael Addition of Metal Alkoxides to -Substituted Alkynylsulfones

The reaction of metal alkoxides with -substituted 2-(p-tolylsulfonyl)acetylenes, involving an anti-Michael addition reaction followed by the in situ elimination of the sulfonyl moiety, provides a direct method for the synthesis of alkyl alkynyl ethers bearing aryl or TIPS groups joined to the triple bond. Arylalkynyl ethers derived from primary alkoxides are in situ hydrolyzed into arylacetic esters.