2024-03-29T11:37:11Zhttps://repositori.uji.es/oai/requestoai:repositori.uji.es:10234/944712023-07-28T10:42:58Zcom_10234_7053com_10234_9col_10234_8639
00925njm 22002777a 4500
dc
Agut Gregori, Juan
author
Vidal-Albalat, Andreu
author
RodrĂguez, Santiago
author
González, Florenci
author
2013-05
We report a highly diastereoselective synthesis of vicinal diamines by the treatment of nitroepoxides with primary amines and then a reducing agent. When using a chiral primary amine, racemic nitroepoxides are transformed into chiral diamines as a single enantiomers (>95:5 er) through a dynamic kinetic asymmetric transformation (DYKAT). The overall process is a one-pot procedure combining the exposure of nitroepoxides to chiral amines to afford diastereomeric mixtures of aminoimines and subsequent stereoselective imine reduction.
AGUT, Juan, et al. Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal Diamines. The Journal of organic chemistry, 2013, 78.11: 5717-5722.
http://hdl.handle.net/10234/94471
http://dx.doi.org/10.1021/jo400501k
Amination
Amines
Epoxy Compounds
Kinetics
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal Diamines