Direct enantioselective reduction of C=C bond of β-polyfluoro-alkylated enones via asymmetric photoredox catalysis
Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we report on the viability of visible light-driven cooperative photoredox and chiral hydrogen-bonding catalysis to effectively address this chall...
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| Published in | Science China. Chemistry Vol. 67; no. 6; pp. 2016 - 2021 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Beijing
Science China Press
01.06.2024
Springer Nature B.V |
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| Abstract | Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we report on the viability of visible light-driven cooperative photoredox and chiral hydrogen-bonding catalysis to effectively address this challenge, as a variety of products are obtained in high yields (up to 85%) with good to excellent enantioselectivities (up to 98% ee). The formation of thermodynamically favorable enol intermediates after double single-electron reduction represents the center of the success. Additionally, the utility of the current method is validated by the convenient regio-specific and -diverse synthesis of various deuterated derivatives for these products using inexpensive D
2
O as the deuterium source. |
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| AbstractList | Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we report on the viability of visible light-driven cooperative photoredox and chiral hydrogen-bonding catalysis to effectively address this challenge, as a variety of products are obtained in high yields (up to 85%) with good to excellent enantioselectivities (up to 98% ee). The formation of thermodynamically favorable enol intermediates after double single-electron reduction represents the center of the success. Additionally, the utility of the current method is validated by the convenient regio-specific and -diverse synthesis of various deuterated derivatives for these products using inexpensive D2O as the deuterium source. Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we report on the viability of visible light-driven cooperative photoredox and chiral hydrogen-bonding catalysis to effectively address this challenge, as a variety of products are obtained in high yields (up to 85%) with good to excellent enantioselectivities (up to 98% ee). The formation of thermodynamically favorable enol intermediates after double single-electron reduction represents the center of the success. Additionally, the utility of the current method is validated by the convenient regio-specific and -diverse synthesis of various deuterated derivatives for these products using inexpensive D 2 O as the deuterium source. |
| Author | Ban, Xu Zhang, Linghong Zhao, Xiaowei Yin, Yanli Ma, Jin Jiang, Zhiyong |
| Author_xml | – sequence: 1 givenname: Linghong surname: Zhang fullname: Zhang, Linghong organization: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University – sequence: 2 givenname: Jin surname: Ma fullname: Ma, Jin organization: School of Chemistry and Chemical Engineering, Henan Normal University, Pingyuan Laboratory – sequence: 3 givenname: Xu surname: Ban fullname: Ban, Xu organization: School of Chemistry and Chemical Engineering, Henan Normal University, Pingyuan Laboratory – sequence: 4 givenname: Xiaowei surname: Zhao fullname: Zhao, Xiaowei organization: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University – sequence: 5 givenname: Yanli surname: Yin fullname: Yin, Yanli organization: School of Chemistry and Chemical Engineering, Henan Normal University, Pingyuan Laboratory, College of Advanced Interdisciplinary Science and Technology, Henan University of Technology – sequence: 6 givenname: Zhiyong surname: Jiang fullname: Jiang, Zhiyong email: jiangzhiyong@htu.edu.cn organization: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, School of Chemistry and Chemical Engineering, Henan Normal University, Pingyuan Laboratory |
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| Snippet | Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we... |
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| SubjectTerms | Alkylation Asymmetry Catalysis Chemistry Chemistry and Materials Science Chemistry/Food Science Deuteration Deuterium Enantiomers Hydrogen bonding Hydrogenation NMR Nuclear magnetic resonance Photoredox catalysis Single electrons Success |
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| Title | Direct enantioselective reduction of C=C bond of β-polyfluoro-alkylated enones via asymmetric photoredox catalysis |
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