183801-41-4Relevant academic research and scientific papers
C2-Symmetric Dinickel Catalysts for Enantioselective [4 + 1]-Cycloadditions
Behlen, Michael J.,Uyeda, Christopher
, p. 17294 - 17300 (2020)
Dinickel naphthyridine-bis(oxazoline) catalysts promote enantioselective intermolecular [4 + 1]-cycloadditions of vinylidene equivalents and 1,3-dienes. The products of this reaction are methylenecyclopentenes, and the exocyclic alkene is generally obtained with high Z selectivity. E- and Z-dienes react in a stereoconvergent fashion, providing cycloadducts with the same sense of absolute stereochemistry and nearly identical ee values. This feature allows dienes that are commercially available as E/Z mixtures to be used as substrates for the cycloaddition. A DFT model for the origin of asymmetric induction is provided.
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Enantioselective Nazarov Cyclizations Catalyzed by an Axial Chiral C6F5-Substituted Boron Lewis Acid
Süsse, Lars,Vogler, Maria,Mewald, Marius,Kemper, Benedict,Irran, Elisabeth,Oestreich, Martin
supporting information, p. 11441 - 11444 (2018/08/28)
A chiral variant of B(C6F5)3 with a 3,3′-disubstituted binaphthyl backbone is shown to catalyze Nazarov cyclizations with high levels of enantio- and diastereocontrol. The parent B(C6F5)3 a
