16174-73-5Relevant academic research and scientific papers
A novel asymmetric vinylogous tin-pummerer rearrangement
Garcia Ruano, Jose Luis,Aleman, Jose,Padwa, Albert
, p. 1757 - 1760 (2004)
Matrix presented. A new type of vinylogous tin-Pummerer rearrangement reaction was observed when benzyl tin derivatives containing a sulfinyl group at the ortho position were allowed to react with acyl chlorides or TPAA. The reaction is thought to proceed by nucleophilic attack of the leaving carboxylate at the γ-position of the conjugated thionium ion. The enantioselectivity (ee) of the reaction can reach values as high as 98%. The observed stereoselectivity is related to the nature of the solvent, the temperature employed, and the stability of the migrating carboxylate anion.
