Stereoselective Synthesis of (E)- and (Z)-2-Alkenyltrimethylsilanes from 1,2-Epoxy-1,3-bis(trimethylsilyl)propane

Article abstract of DOI:10.1246/bcsj.64.1122

Stereoselective synthesis of various (E)- and (Z)-2-alkenyltrimethylsilanes (RCH=CHCH2SiMe3; R=Me, Et, n-Bu, i-Pr, c-hexyl, t-butyl, and phenyl) has been accomplished by a reaction of 1,2-epoxy-1,3-bis(trimethylsilyl)propane with Grignard reagents (RMgX) followed by subsequent Peterson olefination reactions of resulting 1,2-bis(trimethylsilyl)-3-alkanols ; the acid (BF3OEt2 or HClO4)-catalyzed olefination yields the (E)-isomer, while the base (KH or NaH)-induced olefination yields the (Z)-isomer in more than 95 percent stereochemical purity in most cases.