10.1021/jacs.5b09593
The research explores a novel method for the asymmetric synthesis of ?-amino amides through a catalytic enantioconvergent 2-Aza-Cope rearrangement. The purpose of this study is to develop a non-hydrogenative dynamic kinetic resolution (DKR) process for ?-oxo acid derivatives, specifically focusing on a-stereogenic-?-formyl amides. The researchers utilized chiral phosphoric acids as catalysts to facilitate the [3,3]-rearrangement, which concurrently establishes new C-N and C-C bonds and vicinal stereogenic centers. The key chemicals involved include a-stereogenic-?-formyl amides as substrates, allyl amines as reaction partners, and chiral phosphoric acids (such as catalysts A and B) for catalysis. The study concludes that this method achieves high diastereo- and enantiocontrol, producing ?-amino amides that can be further transformed into primary ?-amino amides or reduced to corresponding diamines. The findings represent a rare example of a non-hydrogenative DKR of ?-oxo acid derivatives and demonstrate the potential for generating optically enriched ?-amino acid derivatives with high stereoselectivity, which can be readily converted into functional small molecule building blocks. Future work will focus on delineating the factors that lead to the observed stereoselectivity and applying this knowledge to develop other stereoconvergent reactions involving ?-oxo carboxylic acid derivatives.
10.1021/ja807591m
The research focuses on relay catalysis using a binary catalytic system comprising a ruthenium hydride complex and a Br?nsted acid for a tandem isomerization/carbon-carbon bond formation sequence. The study explores the sequential transformation of allylamides to enamides, then to imine intermediates, and finally to Friedel-Crafts products through a three-step relayed catalysis process. Experiments involved the reaction of variously substituted allylamines with different nucleophilic components under the influence of the binary catalytic system. The research identified optimal acid catalysts for different protecting groups on allylamines and demonstrated the scope of the transformation with a series of substituted allylamines and aromatic compounds. The study also compared the efficiency of the relay catalysis with a control experiment using enamide and highlighted the advantage of using readily available allylamides to generate reactive imines for further transformations. Analytical techniques such as spectroscopic data were used to confirm the structures of the reaction products.
10.1016/j.tetlet.2013.01.021
The research focuses on the solventless, convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles using microwave irradiation. The purpose of this study was to develop a green approach to synthesize 4-substituted-3-cyano-2-aminopyridines, which are important intermediates in organic synthesis and exhibit various biological properties. The methodology is highlighted for its ease of execution, rapid access, and good yields. The chemicals used in the process include various primary amines such as methylamine, allylamine, butylamine, isopropylamine, and benzylamine, which reacted with enaminonitriles to form the desired 2-aminopyridine derivatives. The study concluded that the solvent-free methods, particularly under microwave activation, were efficient and preferred due to shorter reaction times and higher yields, thus opening a new route for the synthesis of various substituted nitrogen heterocycles.
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