Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines

Hung Che Chen; Chi Yun Liu; Venkatachalam Angamuthu; Wei Chen Chen; Chi Sheng Wen; Duen Ren Hou

doi:10.1021/acs.orglett.2c04042

Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines

Hung Che Chen, Chi Yun Liu, Venkatachalam Angamuthu, Wei Chen Chen, Chi Sheng Wen, Duen Ren Hou

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

4 引文斯高帕斯（Scopus）

摘要

A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed. This chiral pool synthesis utilized the skeleton of arabinose to generate diastereomerically pure 2-oxazolidinone-fused aziridines, which underwent ring opening with a fluoride anion. The adducts, polyoxygenated organofluorides, were useful precursors to various fluorinated compounds, such as fluorinated amino acids.

原文	???core.languages.en_GB???
頁（從 - 到）	190-194
頁數	5
期刊	Organic Letters
卷	25
發行號	1
DOIs	https://doi.org/10.1021/acs.orglett.2c04042
出版狀態	已出版 - 13 1月 2023

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10.1021/acs.orglett.2c04042

利用噁唑烷酮與?環丙烷稠環進行不對稱合成
Hou, D.-R. (PI)
1/08/20 → 31/07/21
研究計畫: Research
天然物合成與氮環丙烷相關合成方法之發展(2/2)
Hou, D.-R. (PI)
1/08/19 → 31/07/20
研究計畫: Research

CCDC 2189525: Experimental Crystal Structure Determination
Chen, H.-C. (貢獻者), Liu, C.-Y. (貢獻者), Angamuthu, V. (貢獻者), Chen, W.-C. (貢獻者), Wen, C.-S. (貢獻者) & Hou, D.-R. (貢獻者), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2chcv3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2chcv3&sid=DataCite
資料集

引用此

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title = "Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines",

abstract = "A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed. This chiral pool synthesis utilized the skeleton of arabinose to generate diastereomerically pure 2-oxazolidinone-fused aziridines, which underwent ring opening with a fluoride anion. The adducts, polyoxygenated organofluorides, were useful precursors to various fluorinated compounds, such as fluorinated amino acids.",

author = "Chen, {Hung Che} and Liu, {Chi Yun} and Venkatachalam Angamuthu and Chen, {Wei Chen} and Wen, {Chi Sheng} and Hou, {Duen Ren}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

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doi = "10.1021/acs.orglett.2c04042",

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T1 - Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines

AU - Chen, Hung Che

AU - Liu, Chi Yun

AU - Angamuthu, Venkatachalam

AU - Chen, Wei Chen

AU - Wen, Chi Sheng

AU - Hou, Duen Ren

PY - 2023/1/13

Y1 - 2023/1/13

N2 - A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed. This chiral pool synthesis utilized the skeleton of arabinose to generate diastereomerically pure 2-oxazolidinone-fused aziridines, which underwent ring opening with a fluoride anion. The adducts, polyoxygenated organofluorides, were useful precursors to various fluorinated compounds, such as fluorinated amino acids.

AB - A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed. This chiral pool synthesis utilized the skeleton of arabinose to generate diastereomerically pure 2-oxazolidinone-fused aziridines, which underwent ring opening with a fluoride anion. The adducts, polyoxygenated organofluorides, were useful precursors to various fluorinated compounds, such as fluorinated amino acids.

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U2 - 10.1021/acs.orglett.2c04042

DO - 10.1021/acs.orglett.2c04042

M3 - 期刊論文

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AN - SCOPUS:85145452544

SN - 1523-7060

VL - 25

SP - 190

EP - 194

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines

摘要

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指紋

專案

利用噁唑烷酮與?環丙烷稠環進行不對稱合成

天然物合成與氮環丙烷相關合成方法之發展(2/2)

資料集

CCDC 2189525: Experimental Crystal Structure Determination

引用此