The scandium-catalyzed substitution reactions of the phenylsulfanyl and phenylselanyl propargyl alcohols 3a- i and 7a- h regioselectively proceeded to give the propargylated compounds 4 and 8 in high yields.

C-C bond formation O 0282Scandium-Catalyzed Carbon-Carbon Bond-Forming Reactions of 3-Sulfanyland 3-Selanylpropargyl Alcohols. -The scandium-catalyzed substitution of propargylic alcohols bearing phenylsulfanyl or phenylselanyl groups proceeds with excellent regioselectivity in most cases to give α-branched alkynes, e.g. (III) and (VI), in moderate to high yields. The analogous reaction of alkynylcycloalkanols (VII), however, affords β-elimination and/or allenyl side products. -(YOSHIMATSU*, M.; OTANI, T.; MATSUDA, S.; YAMAMOTO, T.; SAWA, A.; Org. Lett. 10 (2008) 19, 4251-4254; Dep. Chem., Fac. Educ., Gifu Univ., Yanagido, Gifu 501-11, Japan; Eng.) -Mischke 06-051