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Open AccessArticle

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

1
College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 41566, Korea
2
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, Gyeonggi-do 11160, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Narciso M. Garrido
Molecules 2019, 24(24), 4495; https://doi.org/10.3390/molecules24244495
Received: 19 November 2019 / Revised: 1 December 2019 / Accepted: 6 December 2019 / Published: 8 December 2019
(This article belongs to the Special Issue New Synthetic Methods for Organic Compounds)
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. View Full-Text
Keywords: rearrangement; aza-quaternary carbon center; ring expansion rearrangement; aza-quaternary carbon center; ring expansion
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MDPI and ACS Style

Choi, G.; Jo, S.; Mun, J.; Jeong, Y.; Kim, S.-H.; Jung, J.-W. Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers. Molecules 2019, 24, 4495.

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