Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
Open Access
- 8 December 2019
- Vol. 24 (24), 4495
- https://doi.org/10.3390/molecules24244495
Abstract
The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and acyclic substrates underwent the unexpected rearrangement to afford products in moderate to high yields, and (4) the reaction seemed to be highly stereoselective. In addition, a plausible mechanism has been discussed.Funding Information
- National Research Foundation of Korea (NRF-2015M3A9E7029176, NRF-2017R1D1A1B03032798, NRF-2018M3A9A8055212)
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