Stereoselective Stille coupling reactions of 1,1-bis(trialkylstannyl)ethenes

Article abstract of DOI:10.1016/S0040-4039(97)10583-4

Stille coupling of 1,1-bis(tri-n-butylstannyl)ethenes proceeds in a stereoselective manner to afford the E-vinylstannanes. Repetition of this sequence affords a new route to hi-substituted alkenes. Intramolecular Stille coupling of a suitable vinyl bromide affords a pyranyl-derived vinylstannane. In certain cases, with bulky electrophiles, butyl migration rather than that of the sp²-hybridised centre is observed. A working model is put forward in order to rationalise these results.