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Iridium-Catalyzed Asymmetric α-Allylic Alkylation of Amides using Vinyl Azide as Amide Enolate Surrogate

preprint
submitted on 05.08.2020 and posted on 06.08.2020 by Aditya Chakrabarty, Santanu Mukherjee
Among the unstabilized enolates used as nucleophile in iridium-catalyzed asymmetric allylic alkylation reactions, amide enolates are least explored. Vinyl azides are now employed as amide enolate surrogate for the first time in Ir-catalyzed asymmetric allylic alkylation with branched allylic alcohols as the allylic electrophile. Competing reaction pathways are suppressed through systematic tuning of steric and electronic properties of vinyl azide to effect α-allylic alkylation of secondary acetamides with high atom-economy, exclusive branched selectivity and moderate to excellent enantioselectivity.

Funding

Science and Engineering Research Board (SERB): EMR/2016/005045

Council of Scientific and Industrial Research (CSIR): 02(0385)/19/EMR-II

Department of Science and Technology (DST)-FIST: SR/FST/CS II-040/2015

History

Email Address of Submitting Author

sm@iisc.ac.in

Institution

Indian Institute of Science, Bangalore

Country

India

ORCID For Submitting Author

0000-0001-9651-6228

Declaration of Conflict of Interest

The authors declare no competing financial interest

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