70094-92-7Relevant academic research and scientific papers
Cooperative catalysis by palladium and a chiral phosphoric acid: Enantioselective amination of racemic allylic alcohols
Banerjee, Debasis,Junge, Kathrin,Beller, Matthias
, (2014)
Cooperative catalysis by [Pd(dba)2] and the chiral phosphoric acid BA1 in combination with the phosphoramidite ligand L8 enabled the efficient enantioselective amination of racemic allylic alcohols with a variety of functionalized amines. This
Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines
Kim, Seung Wook,Schwartz, Leyah A.,Zbieg, Jason R.,Stivala, Craig E.,Krische, Michael J.
supporting information, p. 671 - 676 (2019/01/08)
The air- and water-stable π-allyliridium C,O-benzoate modified by (S)-tol-BINAP, (S)-Ir-II, catalyzes highly regio- and enantioselective Tsuji-Trost-type aminations of racemic branched alkyl-substituted allylic acetates using primary or secondary (hetero)aromatic amines. Specifically, in the presence of (S)-Ir-II (5 mol%) in DME solvent at 60-70 °C, α-methyl allyl acetate 1a (100 mol%) reacts with primary (hetero)aromatic amines 2a-2l (200 mol%) or secondary (hetero)aromatic amines 3a-3l (200 mol%) to form the branched products of allylic amination 4a-4l and 5a-5l, respectively, as single regioisomers in good to excellent yield with uniformly high levels of enantioselectivity. As illustrated by the conversion of heteroaromatic amine 3m to adducts 6a-6g, excellent levels of regio- and enantioselectivity are retained across diverse branched allylic acetates bearing normal alkyl or secondary alkyl substituents. For reactants 3n-3p, which incorporate both primary and secondary aryl amine moieties, regio- and enantioselective amination occurs with complete site-selectivity to furnish adducts 7a-7c. Mechanistic studies involving amination of the enantiomerically enriched, deuterium-labeled acetate 1h corroborate C-N bond formation via outer-sphere addition.
Regioselective iron-catalyzed allylic amination
Plietker, Bernd
, p. 6053 - 6056 (2007/10/03)
(Chemical Equation Presented) Iron age: An air- and water-resistant iron(-II) catalyst, in the presence of triphenylphosphane under buffered conditions, allows for the highly regioselective and stereoselective allylation of primary aromatic amines. A broa
