Tetrahedron Letters p. 485 - 488 (1998)
Update date:2022-08-29
Topics:
Quayle, Peter
Wang, Jingyang
Xu, Jie
Urch, Christopher J.
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.
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