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...

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Autores principales: Itoh, Kennosuke, Odate, Fumiya, Karikomi, Takuma, Obe, Keishi, Miyamori, Tsutomu, Kamiya, Hideaki, Yoza, Kenji, Nagai, Kenichiro, Fujii, Hideaki, Suga, Hiroyuki, Tokunaga, Ken
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
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.
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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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