Efficient synthesis of novel 2-spiropiperidines including an unprecedented non-symmetrical 2,6-bis-spiropiperidine

[Display omitted] Tertiary-alkyl substituted δ-amino-β-ketoesters can be readily prepared from β-amino acids, which can then undergo condensation with aldehydes to furnish novel, highly substituted 2-spiropiperidines. The method allows access to conformationally distinct structural- and regio-isomer...

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Bibliographic Details
Published in:Tetrahedron letters 2021-02, Vol.65, p.152752, Article 152752
Main Authors: McQueen, Thomas M., Griggs, Samuel D.
Format: Article
Language:English
Subjects:
Amino-β-ketoester
Medicinal Chemistry
Spirocycle
Spirooxetane
Spiropiperidine
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Summary:[Display omitted] Tertiary-alkyl substituted δ-amino-β-ketoesters can be readily prepared from β-amino acids, which can then undergo condensation with aldehydes to furnish novel, highly substituted 2-spiropiperidines. The method allows access to conformationally distinct structural- and regio-isomers of previously reported 2-spiropiperidines, and further expands the potential to explore three-dimensional chemical space. Using 3-oxetanone as the electrophile yielded the first example of a synthetically challenging non-symmetrical 2,6-bis-spiropiperidine.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152752