108915-07-7Relevant academic research and scientific papers
Modular synthesis of amine-functionalized oxazolines
Rajaram, Sridhar,Sigman, Matthew S.
, p. 3399 - 3401 (2002)
(matrix presented) Substituted oxazoline amines have been prepared in high yield from β-amino alcohols and Fmoc-protected α-amino acids using CCl4, PPh3, and HUnig's base in a one-pot procedure followed by base-mediated deprotection.
Parallel screening of asymmetric bidentate ligands in zinc catalyzed transfer hydrogenation
Zaman, Tariq,Nasir, Habib,Bergin, Enda
, p. 85 - 90 (2014/05/06)
Development in the field of asymmetric catalysis is driven by the importance of stereochemically pure compounds in the field of pharmaceutical industry, agrochemicals and flavors. The unpredictable results given by new catalysts make the design of effecti
Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
Malkov, Andrei V.,Stewart-Liddon, Angus J. P.,McGeoch, Grant D.,Ramirez-Lopez, Pedro,Kocovsky, Pavel
scheme or table, p. 4864 - 4877 (2012/07/28)
A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).
Synthesis of amine functionalized oxazolines with applications in asymmetric catalysis
Miller, Jeremie J.,Rajaram, Sridhar,Pfaffenroth, Cornelia,Sigman, Matthew S.
experimental part, p. 3110 - 3119 (2009/09/05)
This paper describes the synthesis of three classes of amine functionalized oxazolines that have been successfully used in asymmetric catalysis in our laboratory. Failed synthetic routes and significantly improved procedures are discussed including the synthesis of ligands for Nozaki-Hiyama-Kishi (NHK) carbonyl allylation reactions that do not require chromatography for purification.
Asymmetric Catalysis, 45. - Enantioselective Hydrosilylation of Ketones with 2/Pyridinyloxazoline Catalysts
Brunner, Henri,Obermann, Uwe
, p. 499 - 508 (2007/10/02)
21 optically active 2-(2-pyridinyl)oxazolines are synthesized from 2-cyanopyridine and optically pure amino alcohols.The new pyridinyloxazolines are used as cocatalysts together with 2 as homogeneous in situ catalysts in the enantioselective hydrosilylation of prochiral ketones with diphenylsilane.After hydrolysis, 1-phenylethanol is produced in 83.4percent ee from acetophenone.Another three ketones are included into these investigations.The optical purity depends on the rhodium/ligand, rhodium/ketone, and ketone/silane ratio as well as on the solvent.Compared with other organic solvents, hydrosilylations in the solvent CCl4 without exceptions result in better chemical yields and optical purities as consequence of a change in the catalytically active species due to oxidative addition of CCl4. - Keywords: Enantioselective hydrosilylation/ Optically active secondary alcohols/ Rhodium/ pyridinyloxazoline catalysts
