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

Goyeong Choi; Seoyoung Jo; Juyeon Mun; Yonguk Jeong; Seok Ho Kim; Jong Wha Jung

doi:10.3390/molecules24244495

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

Goyeong Choi, Seoyoung Jo, Juyeon Mun, Yonguk Jeong, Seok Ho Kim, Jong Wha Jung

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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.

Original language	English
Article number	4495
Journal	Molecules
Volume	24
Issue number	24
DOIs	https://doi.org/10.3390/molecules24244495
State	Published - 8 Dec 2019

Keywords

Aza-quaternary carbon center
Rearrangement
Ring expansion

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10.3390/molecules24244495

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

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.",

keywords = "Aza-quaternary carbon center, Rearrangement, Ring expansion",

author = "Goyeong Choi and Seoyoung Jo and Juyeon Mun and Yonguk Jeong and Kim, {Seok Ho} and Jung, {Jong Wha}",

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T1 - Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

AU - Choi, Goyeong

AU - Jo, Seoyoung

AU - Mun, Juyeon

AU - Jeong, Yonguk

AU - Kim, Seok Ho

AU - Jung, Jong Wha

PY - 2019/12/8

Y1 - 2019/12/8

N2 - 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.

AB - 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.

KW - Aza-quaternary carbon center

KW - Rearrangement

KW - Ring expansion

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

Abstract

Keywords

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