Enantioselective Synthesis of Acenaphthene-Type Monohydrosilanes
Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)–H silylation for enantioselective synthes...
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| Published in | Organic letters Vol. 27; no. 14; pp. 3622 - 3630 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
11.04.2025
Amer Chemical Soc |
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| Abstract | Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)–H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. |
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| AbstractList | Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp³)–H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)-H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity.Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)-H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp )-H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)-H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C(sp3)–H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity. |
| Author | Zhu, Xinrui Mu, Delong Chen, Jiean |
| AuthorAffiliation | Pingshan Translational Medicine Center |
| AuthorAffiliation_xml | – name: Pingshan Translational Medicine Center |
| Author_xml | – sequence: 1 givenname: Delong surname: Mu fullname: Mu, Delong email: mudl@szbl.ac.cn organization: Pingshan Translational Medicine Center – sequence: 2 givenname: Xinrui surname: Zhu fullname: Zhu, Xinrui organization: Pingshan Translational Medicine Center – sequence: 3 givenname: Jiean orcidid: 0000-0003-0703-5831 surname: Chen fullname: Chen, Jiean email: chenja@szbl.ac.cn organization: Pingshan Translational Medicine Center |
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| Snippet | Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted... |
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| SubjectTerms | Chemistry Chemistry, Organic enantioselective synthesis enantioselectivity heterocyclic compounds insecticidal properties materials science Physical Sciences Science & Technology silicon silylation |
| Title | Enantioselective Synthesis of Acenaphthene-Type Monohydrosilanes |
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