Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 19, Pages 6496-6500Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600823
Keywords
3D space; dearomatisation; lead identification; N-acyliminium ions; spirocycles
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Funding
- EPSRC [EP/J016128/1]
- University of York
- Engineering and Physical Sciences Research Council [EP/J016128/1] Funding Source: researchfish
- EPSRC [EP/J016128/1] Funding Source: UKRI
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Heteroaromatic carboxylic acids have been directly coupled with imines using propylphosphonic anhydride (T3P) and NEt(iPr)(2) to form azaspirocycles via intermediate N-acyliminium ions. Spirocyclic indolenines (3H-indoles), azaindolenines, 2H-pyrroles and 3H-pyrroles were all accessed using this metal-free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under-represented in existing drugs and high throughput screening libraries.
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