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

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 c...

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Autores principales: Choi, Goyeong, Jo, Seoyoung, Mun, Juyeon, Jeong, Yonguk, Kim, Seok-Ho, Jung, Jong-Wha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943665/
https://www.ncbi.nlm.nih.gov/pubmed/31817984
http://dx.doi.org/10.3390/molecules24244495
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author Choi, Goyeong
Jo, Seoyoung
Mun, Juyeon
Jeong, Yonguk
Kim, Seok-Ho
Jung, Jong-Wha
author_facet Choi, Goyeong
Jo, Seoyoung
Mun, Juyeon
Jeong, Yonguk
Kim, Seok-Ho
Jung, Jong-Wha
author_sort Choi, Goyeong
collection PubMed
description 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.
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spelling pubmed-69436652020-01-10 Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers Choi, Goyeong Jo, Seoyoung Mun, Juyeon Jeong, Yonguk Kim, Seok-Ho Jung, Jong-Wha Molecules Article 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. MDPI 2019-12-08 /pmc/articles/PMC6943665/ /pubmed/31817984 http://dx.doi.org/10.3390/molecules24244495 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Choi, Goyeong
Jo, Seoyoung
Mun, Juyeon
Jeong, Yonguk
Kim, Seok-Ho
Jung, Jong-Wha
Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title_full Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title_fullStr Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title_full_unstemmed Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title_short Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers
title_sort unexpected rearrangement of n-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides to construct aza-quaternary carbon centers
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943665/
https://www.ncbi.nlm.nih.gov/pubmed/31817984
http://dx.doi.org/10.3390/molecules24244495
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