309271-26-9Relevant academic research and scientific papers
Iridium-catalyzed asymmetric isomerization of primary allylic alcohols
Mantilli, Luca,Gerard, David,Torche, Sonya,Besnard, Celine,Mazet, Clement
supporting information; experimental part, p. 5143 - 5147 (2009/12/07)
Nothing to sm(Ir)k at: Under appropriate reaction conditions, iridium hydride catalysts promote the isomerization of primary allylic alcohols. The best catalysts, like (R)-1 (P green, O red, N blue, Ir yellow), deliver the desired chiral aldehydes with excellent enantioselectivity and good yields. Mechanistic hypotheses have been developed on the basis of preliminary investigations.
First rhodium/phosphoramidite complex-catalyzed enantioselective isomerization of allylic alcohols into aldehydes
Boeda, Fabien,Mosset, Paul,Crévisy, Christophe
, p. 5021 - 5024 (2007/10/03)
Primary allylic alcohols are converted into chiral aldehydes in the presence of a catalytic amount (7 mol %) of a monodentate phosphoramidite rhodium catalyst. The aldehydes are isolated in high yields (84-89%) and moderate to good ee's (38-70%). A preliminary mechanistic study showed that the reaction proceeds through a 1,3-H migration pathway.
A versatile new catalyst for the enantioselective isomerization of allylic alcohols to aldehydes: Scope and mechanistic studies
Tanaka, Ken,Fu, Gregory C.
, p. 8177 - 8186 (2007/10/03)
A new planar-chiral bidentate phosphaferrocene ligand (2) has been synthesized and structurally characterized. The derived rhodium complex, [Rh(cod)(2)]BF4, serves as an effective catalyst for asymmetric isomerizations of allylic alcohols to aldehydes, furnishing improved yields, scope, and enantioselectivities relative to previously reported methods. The catalyst is air-stable and can be recovered at the end of the reaction. Mechanistic studies establish that the isomerization proceeds via an intramolecular 1,3-hydrogen migration and that the catalyst differentiates between the enantiotopic C1 hydrogens.
