Dynamic kinetic asymmetric ring-opening/reductive amination sequence of racemic nitroepoxides with chiral amines: enantioselective synthesis of chiral vicinal diamines

Agut, J.; Vidal, A.; Rodríguez, S.; González, F.V.

Journal of Organic Chemistry 78(11): 5717-5722


ISSN/ISBN: 1520-6904
PMID: 23641667
DOI: 10.1021/jo400501k
Accession: 052735372

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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.