Synthesis of Novel Angular Spirocyclic Azetidines

The syntheses of a variety of novel angular azaspiro[3.3]heptanes are reported. gem-Difluoro and gem-dimethyl variants of the angular 1,6-diazaspiro[3.3]heptane module were prepared in high yields using efficient sequences. Additionally, a practical one-pot synthesis of 5-oxo-2-azaspiro[3.3]heptanes...

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Bibliographic Details
Published in:Organic letters 2011-02, Vol.13 (4), p.780-783
Main Authors: Guérot, Carine, Tchitchanov, Boris H, Knust, Henner, Carreira, Erick M
Format: Article
Language:English
Subjects:
Azetidines - chemical synthesis
Azetidines - chemistry
Heptanes - chemical synthesis
Heptanes - chemistry
Molecular Structure
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The syntheses of a variety of novel angular azaspiro[3.3]heptanes are reported. gem-Difluoro and gem-dimethyl variants of the angular 1,6-diazaspiro[3.3]heptane module were prepared in high yields using efficient sequences. Additionally, a practical one-pot synthesis of 5-oxo-2-azaspiro[3.3]heptanes and subsequent conversions into functionalized derivatives are described. The methods reported are amenable to the synthesis of these building blocks for drug discovery as members of a library or individually on a preparative scale.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol103050c