100017-28-5Relevant 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
, 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.
Stereoselective synthesis of furans by the Pd-catalyzed Oshima-Utimoto reaction
Evans, Michael A.,Morken, James P.
, p. 3367 - 3370 (2007/10/03)
(Chemical Equation Presented) The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.
Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation
Gazzard, Lewis J.,Motherwell, William B.,Sandham, David A.
, p. 979 - 993 (2007/10/03)
Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.