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From Heteroaromatic acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
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Chambers_et_al-2016-Chemistry_-_A_European_Journal
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| Journal | Chemistry : A European Journal (Weinheim an der Bergstrasse, Germany) |
|---|---|
| Date | Accepted/In press - 22 Feb 2016 |
| Date | E-pub ahead of print - 25 Feb 2016 |
| Date | Published (current) - 2016 |
| Issue number | 19 |
| Volume | 22 |
| Number of pages | 5 |
| Pages (from-to) | 6496-6500 |
| Early online date | 25/02/16 |
| Original language | English |
Abstract
Heteroaromatic carboxylic acids have been directly coupled with imines using T3P and NEt(i-Pr)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.
Bibliographical note
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
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