Synthesis, characterization, and nucleophilic ring opening reactions of cyclohexyl-substituted β-haloamines and aziridinium ions

[Display omitted] Cyclohexyl-substituted β-haloamines and aziridinium ions were prepared and characterized. Stereospecific ring opening of aziridinium ions was applied for efficient synthesis of vicinal amine, β-amino acid, and tetrahydroisoquinoline (THIQ) analogues. Nucleophilic ring opening react...

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Bibliographic Details
Published in:Tetrahedron letters 2015-02, Vol.56 (7), p.946-948
Main Authors: Chong, Hyun-Soon, Sun, Xiang, Chen, Yunwei, Wang, Meng
Format: Article
Language:English
Subjects:
Amines
Aziridinium ion
Friedel–Crafts reaction
Ring opening
Strained ring
Synthesis (chemistry)
Tetrahedrons
Tetrahydroisoquinoline
β-Haloamines
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Summary:[Display omitted] Cyclohexyl-substituted β-haloamines and aziridinium ions were prepared and characterized. Stereospecific ring opening of aziridinium ions was applied for efficient synthesis of vicinal amine, β-amino acid, and tetrahydroisoquinoline (THIQ) analogues. Nucleophilic ring opening reactions of aziridinium ions and N-protected aziridine analogues were for the first time comparatively studied. The result of nucleophilic reactions clearly indicates that aziridinium ions were significantly more reactive toward nucleophilic ring opening than the aziridine analogues.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.12.101