169172-22-9Relevant articles and documents
Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude
Fegyverneki, Dániel,Kolozsvári, Natália,Molnár, Dániel,Egyed, Orsolya,Holczbauer, Tamás,Soós, Tibor
supporting information, p. 2179 - 2183 (2019/01/04)
The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.