815575-18-9Relevant academic research and scientific papers
Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes
Chu, John C. K.,Dalton, Derek M.,Rovis, Tomislav
supporting information, p. 4445 - 4452 (2015/04/14)
We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due to limiting the undesired coordination of 1-azadiene to the Lewis acid and thus allowing the reaction to be carried out at lower temperature. A series of secondary kinetic isotope effect studies using a range of ligands implicates a stepwise mechanism for the transformation, involving an initial Michael-type addition of the imine to the nitro-alkene followed by a cyclization event. The stepwise mechanism obviates the electronic requirement inherent to a concerted mechanism, explaining the successful cycloaddition between two electron-deficient partners. (Chemical Equation Presented).
Chiral lanthanide complexes: Coordination chemistry, spectroscopy, and catalysis
Bennett, Stacey D.,Core, Bryony A.,Blake, Matthew P.,Pope, Simon J. A.,Mountford, Philip,Ward, Benjamin D.
supporting information, p. 5871 - 5885 (2014/04/03)
The coordination chemistry and catalytic applications of organometallic and related lanthanide complexes bearing chiral oxazoline ligands is an area that has been largely underdeveloped, in comparison to complexes based upon lanthanide triflates for use i
Near-IR luminescent neodymium complexes: Spectroscopic probes for hydroamination catalysis
Bennett, Stacey D.,Pope, Simon J. A.,Ward, Benjamin D.
supporting information, p. 6072 - 6074 (2013/07/19)
Neodymium complexes bearing the sensitising bis(oxazolinylphenyl)amine (BOPA) ligands have been prepared, and analysed spectroscopically under both catalytic and pseudo-catalytic conditions with respect to the intramolecular hydroamination of an aminoalke
Facile synthesis of C2-symmetric tridentate bis(thiazoline) and bis(oxazoline) ligands and their application in the enantioselective Henry reaction
Lu, Shao-Feng,Du, Da-Ming,Zhang, Shi-Wei,Xu, Jiaxi
, p. 3433 - 3441 (2007/10/03)
A series of novel C2-symmetric bis(thiazoline) ligands with a diphenylamine backbone as a linkage between two thiazoline rings were synthesized by the use of the simple reagent phosphorus pentasulfide. Their application in the catalytic asymmet
