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Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary
A novel asymmetric photodimerization reaction of coumarin derivatives bearing the (S)-4-benzyl-2-oxazolidinone auxiliary provides only the syn-head-to-tail (syn-HT) dimer with moderate diastereoselectivity (up to 75 : 25). The mechanism of complete syn-HT selectivity and moderate diastereoselectivit...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063662/ https://www.ncbi.nlm.nih.gov/pubmed/35515875 http://dx.doi.org/10.1039/c9ra00822e |
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author | Itoh, Kennosuke Odate, Fumiya Karikomi, Takuma Obe, Keishi Miyamori, Tsutomu Kamiya, Hideaki Yoza, Kenji Nagai, Kenichiro Fujii, Hideaki Suga, Hiroyuki Tokunaga, Ken |
author_facet | Itoh, Kennosuke Odate, Fumiya Karikomi, Takuma Obe, Keishi Miyamori, Tsutomu Kamiya, Hideaki Yoza, Kenji Nagai, Kenichiro Fujii, Hideaki Suga, Hiroyuki Tokunaga, Ken |
author_sort | Itoh, Kennosuke |
collection | PubMed |
description | A novel asymmetric photodimerization reaction of coumarin derivatives bearing the (S)-4-benzyl-2-oxazolidinone auxiliary provides only the syn-head-to-tail (syn-HT) dimer with moderate diastereoselectivity (up to 75 : 25). The mechanism of complete syn-HT selectivity and moderate diastereoselectivity is proposed based on the result of density functional theory (DFT) calculation. The benzyl group of the (S)-4-benzyl-2-oxazolidinone auxiliary in combination with a Lewis acid exerts effective diastereofacial shielding of the reaction site. |
format | Online Article Text |
id | pubmed-9063662 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90636622022-05-04 Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary Itoh, Kennosuke Odate, Fumiya Karikomi, Takuma Obe, Keishi Miyamori, Tsutomu Kamiya, Hideaki Yoza, Kenji Nagai, Kenichiro Fujii, Hideaki Suga, Hiroyuki Tokunaga, Ken RSC Adv Chemistry A novel asymmetric photodimerization reaction of coumarin derivatives bearing the (S)-4-benzyl-2-oxazolidinone auxiliary provides only the syn-head-to-tail (syn-HT) dimer with moderate diastereoselectivity (up to 75 : 25). The mechanism of complete syn-HT selectivity and moderate diastereoselectivity is proposed based on the result of density functional theory (DFT) calculation. The benzyl group of the (S)-4-benzyl-2-oxazolidinone auxiliary in combination with a Lewis acid exerts effective diastereofacial shielding of the reaction site. The Royal Society of Chemistry 2019-04-23 /pmc/articles/PMC9063662/ /pubmed/35515875 http://dx.doi.org/10.1039/c9ra00822e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Itoh, Kennosuke Odate, Fumiya Karikomi, Takuma Obe, Keishi Miyamori, Tsutomu Kamiya, Hideaki Yoza, Kenji Nagai, Kenichiro Fujii, Hideaki Suga, Hiroyuki Tokunaga, Ken Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title | Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title_full | Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title_fullStr | Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title_full_unstemmed | Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title_short | Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
title_sort | novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063662/ https://www.ncbi.nlm.nih.gov/pubmed/35515875 http://dx.doi.org/10.1039/c9ra00822e |
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