Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of α-chloroketones

Angewandte Chemie - International Edition

Volumn 46, Issue 20, 2007, Pages 3722-3724

  Malkov, Andrei V ^a   Stončius, Sigitas ^a   Kočovský, Pavel ^a  

^a University of Strathclyde   (United Kingdom)

Author keywords

Amination; Asymmetric synthesis; Aziridines; Organocatalysis; Reduction

Indexed keywords

AMINATION; AMINO ACIDS; BIOCONVERSION; CATALYSIS; ENANTIOSELECTIVITY; ORGANIC COMPOUNDS; REDUCTION; SILICON COMPOUNDS;

ASYMMETRIC SYNTHESIS; AZIRIDINES; ORGANOCATALYSIS;

ENANTIOMERS;

AZIRIDINE DERIVATIVE; KETONE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMINATION; AZIRIDINES; CATALYSIS; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 34250807821     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700165     Document Type: Article

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47. On several occasions (Table 1, entries 3, 7, 10-12, 16, and 17), we could not determine the enantiopurity of aziridines by using HPLC on a chiral stationary phase. However, in all other cases, we were able to show that the enantiopurity of 4 reflected that of 3 (Table 1, entries 1, 2, 4, 6, 8, 9, and 13); therefore, the same behavior can be expected for the rest of the series. Conversely, we could not establish the enantiopurity of the amines 3 m and 3n, though this can be inferred from the enantiopurity of aziridines 4m and 4n, obtained by their cyclization (Table 1, entries 14 and 15).