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ChemRxiv_Mukherjee et al.pdf (1.2 MB)

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

preprint
submitted on 05.08.2020, 15:10 and posted on 06.08.2020, 12:57 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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