Studies on Hydrozirconation of 1-Alkynyl Sulfoxides or Sulfones and the Application for the Synthesis of Stereodefined Vinyl Sulfoxides or Sulfones.

The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with Cp[sub 2]Zr(H)Cl in THF at room temperature predominantly gave Z-β-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-β-halovinyl sulfones, Z-β-sulfonyl α,β-unsaturated ketones, and Z-β-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction. [ABSTRACT FROM AUTHOR]