STEREOSELECTIVE SYNTHESIS OF (Z)-KETENE SELENOTHIOACETALES VIA HYDROZIRCONATION OF LITHIUM ALKYNYLSELENOLATE ANIONS

Abstract

Lithium alkynylselenolate anions react completely with 1.0 equiv of Cp₂Zr(H)Cl in THF at room temperature to give exclusively the α-zirconated vinylselenolate intermediates 3, which by treatment with an alkyl halide afforded the α-zirconated vinyl alkylselenides intermediates 4. Reaction of 4 with alkylsulfenyl chlorides results in the formation of (Z)-ketene selenothioacetals 5 with total control of the regio- and stereochemistry.

Acknowledgments