New Methodology for the Conversion of Epoxides to Alkenes
作者:Feng-Ling Wu、Benjamin P. Ross、Ross P. McGeary
DOI:10.1002/ejoc.200901264
日期:2010.4
Epoxides have been transformed in good yields to alkenes by a process involving (i) ring-opening of the epoxide with 2-mercaptobenzothiazole, (ii) oxidation of the derived s-hydroxy thioethers to the corresponding sulfones, and (iii) thermal or base-promoted fragmentation of these sulfones to alkenes. The stereochemistry of the starting epoxide is transfer-red faithfully to the alkene product, because
An efficient copper‐catalyzed trifluoromethylation of trisubstituted allylic and homoallylicalcohols with Togni’s reagent has been developed. This strategy, accompanied by a double‐bond migration, leads to various branched CF3‐substituted alcohols by using readily available trisubstituted cyclic/acyclic alcohols as substrates. Moreover, for alcohols in which β‐H elimination is prohibited, CF3‐containing
addition of alkylcopper compounds to 1-alkynes, are transformed with retention to various ethylenic structures; 1-deutero-1-alkenes, symmetrical conjugated dienes, 1-iodo-1-alkenes, di- or tri-substituted alkenes and primary or secondary allylic alcohols.