Abstract
An efficient, highly stereoconservative synthesis has been developed for the preparation of aniline derived 1-arylpyrrole-2-carboxamide atropisomers using diphenylphosphoryl azide (DPPA). The classical azide synthesis, involving reaction with active acylating agents prepared from axially chiral benzoic acid derivatives, showed significant racemization caused by intramolecular tricyclic isoimidium salt formation. In order to avoid the ring closure reaction, the azide synthesis was carried out with DPPA in a stereoconservative manner, and Curtius rearrangement followed by hydrolysis resulted in enantiopure products. The application of the novel racemisation-free synthetic method of axially chiral anilines from atropisomeric benzoic acid derivatives is demonstrated by the preparation of secondary as well as tertiary amines containing 2-(2-substituted-1H-pyrrole-1-yl)aniline type diamines.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
