1042929-99-6Relevant academic research and scientific papers
One-pot, two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazoles
Kuang, Lu,Ming, Peng,Wan, Chang-Feng,Chen, Jun-Min,Sheng, Shou-Ri
, p. 563 - 569 (2021)
A facile, one-pot two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives has been developed. The protocol employs an N-allylation of N-propargylated amines with 2,3-dibromopropene in the presence of K2CO3 in DMSO and a CuI-catalyzed [3 + 2] cycloaddition reaction of the synthetic N-(2-bromoallyl)-N-propargyl amines with sodium azide sequentially. Such a method provides methylene-substituted 1,2,3-triazole fused piperazines with some advantages such as simple operation, high efficiency and good product yield (80–91%) through readily available starting materials.
Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary
Buzzetti, Luca,Puri??, Mikus,Greenwood, Phillip D. G.,Waser, Jerome
supporting information, p. 17334 - 17339 (2020/11/02)
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity of chemical reactions. Asymmetric catalysis is used to install a transient chiral auxiliary starting from achiral precursors, which then directs diastereoselective reactions. We apply this strategy to a palladium-catalyzed carboetherification/hydrogenation sequence on propargylic amines, providing fast access to enantioenriched chiral amino alcohols, important building blocks for medicinal chemistry and drug discovery. All stereoisomers of the product could be accessed by the choice of ligand and substituent on the propargylic amine, leading to a stereodivergent process.
