SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED BUTA-1,2,3-TRIENES

Reaction of the lithium or cerium(III) anion of 3-alkyl or 3-aryl Substituted 3-trimethylsilylprop-1-yne 1 with aldehydes or ketones afforded 1-hydroxy-4-trimethylsilylbut-2-ynes 2 in good yields. Conversion of the silyl prop-2-ynylic alcohols 2 into the corresponding acetates 3 followed by tetrabutylammonium fluoride-induced. 1,4-elimination gave alkyl-and aryl substituted buta-1,2,3-trienes 4 in good yields.