160093-24-3Relevant articles and documents
Pd-Catalyzed Arylation of 1,2-Amino Alcohol Derivatives via β-Carbon Elimination
Martin, Ruben,Pericàs, Miquel A.,Sau, Miriam
supporting information, p. 52 - 56 (2021/12/29)
Herein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to β-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope including challenging substrate combinations even in an enantioselective manner.
Gallium-Catalyzed Scriabine Reaction
Pareek, Manish,Bour, Christophe,Gandon, Vincent
supporting information, p. 6957 - 6960 (2018/11/21)
γ-Aryl enol acetates are easily obtained from diacetoxy alkenes and electron-rich arenes at room temperature using GaCl3 as catalyst. The products can then be converted into β-aryl aldehydes. This method represents the first broadly applicable catalytic version of the Scriabine reaction. DFT computations shed light on the mechanism of this transformation.
Generality and Mechanism of Homobenzylic-Homoallylic Hydrogenolysis of 5-Aryl-4,5-dihydro-1,3-dioxepins
Samizu, Kiyohiro,Ogasawara, Kunio
, p. 7989 - 7992 (2007/10/02)
Birch reduction of several 5-aryl-4,5-dihydro-1,3-dioxepins gave rise to 3-arylbutanal in moderate to good yields by hydrogenolytic cleavage of the homobenzylic-homoallylic carbon-oxygen bond when the benzylic-allylic carbon is tertiary.However, the reaction did not take place when the benzylic-allylic carbon is quaternary.Moreover, the reaction was found to proceed with complete racemization at the benylic-allylic center indicating a concurrent elimination-reduction pathway to be involved.
