《Catalytic Regioselective Isomerization of 2,2-Disubstituted Oxetanes to Homoallylic Alcohols》 was written by Cabre, Albert; Rafael, Sergi; Sciortino, Giuseppe; Ujaque, Gregori; Verdaguer, Xavier; Lledos, Agusti; Riera, Antoni. Electric Literature of C3H9IOS And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:
The selective isomerization of strained heterocyclic compounds is an important tool in organic synthesis. An unprecedented regioselective isomerization of 2,2-disubstituted oxetanes into homoallylic alcs. is described. The use of tris(pentafluorophenyl)borane (B(C6F5)3), a com. available Lewis acid was key to obtaining good yields and selectivities since other Lewis acids afforded mixtures of isomers and substantial polymerization The reaction took place under exceptionally mild reaction conditions and very low catalyst loading (0.5 mol %). DFT calculations disclose the mechanistic features of the isomerization and account for the high selectivity displayed by the B(C6F5)3 catalyst. The synthetic applicability of the new reaction is demonstrated by the preparation of γ-chiral alcs. using iridium-catalyzed asym. hydrogenation. In the experiment, the researchers used Trimethylsulfoxonium iodide(cas: 1774-47-6Electric Literature of C3H9IOS)
Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides.Electric Literature of C3H9IOS
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com