Ontology highlight
ABSTRACT:
SUBMITTER: Chambers SJ
PROVIDER: S-EPMC5071705 | biostudies-other | 2016 May
REPOSITORIES: biostudies-other
Chambers Sarah J SJ Coulthard Graeme G Unsworth William P WP O'Brien Peter P Taylor Richard J K RJ
Chemistry (Weinheim an der Bergstrasse, Germany) 20160323 19
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 exis ...[more]