80581-44-8Relevant academic research and scientific papers
Syntheses of new chiral phosphane ligands by diastereoselective conjugate addition of phosphides to enantiomerically pure acceptor-substituted olefins from the chiral pool
Wiese, Burkhard,Knuehl, Guido,Flubacher, Dietmar,Priess, Jan W.,Ulriksen, Bolette,Broedner, Kerstin,Helmchen, Guenter
, p. 3246 - 3262 (2005)
A variety of new chiral phosphanes were prepared by highly diastereoselective additions of phosphanes to α,β-unsaturated carbonyl compounds and related acceptor-substituted olefins derived from myrtenal as ex chiral pool source. Monophosphanes with astereogenic as well as stereogenic phosphorus are described. In addition diphosphanes were prepared by a highly diastereoselective double conjugate addition of a secondary diphosphane. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
, p. 6482 - 6490 (2012/10/30)
The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
