Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal Diamines
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Other documents of the author: Agut Gregori, Juan; Vidal-Albalat, Andreu; Rodríguez, Santiago; González, Florenci
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http://dx.doi.org/10.1021/jo400501k |
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Title
Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal DiaminesDate
2013-05Publisher
American Chemical SocietyBibliographic citation
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.Type
info:eu-repo/semantics/articlePublisher version
http://pubs.acs.org/doi/abs/10.1021/jo400501kSubject
Abstract
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 trans ... [+]
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. [-]
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J. Org. Chem., 2013, 78 (11)Rights
© 2013 American Chemical Society
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