Facile access to bicyclo[2.1.1]hexanes by Lewis acid-catalyzed formal cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes
Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron...
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| Published in | Nature communications Vol. 15; no. 1; pp. 6128 - 9 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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London
Nature Publishing Group UK
20.07.2024
Nature Publishing Group Nature Portfolio |
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| Abstract | Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible.
Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. Here, the authors present facile access to a variety of bicyclo[2.1.1]hexanes via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes under Lewis acid catalysis. |
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| AbstractList | Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible.Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. Here, the authors present facile access to a variety of bicyclo[2.1.1]hexanes via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes under Lewis acid catalysis. Abstract Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible. Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible. Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible. Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. Here, the authors present facile access to a variety of bicyclo[2.1.1]hexanes via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes under Lewis acid catalysis. |
| ArticleNumber | 6128 |
| Author | Deng, Li Hu, Sai Pan, Yuming Ni, Dongshun |
| Author_xml | – sequence: 1 givenname: Sai surname: Hu fullname: Hu, Sai organization: Department of Chemistry, Zhejiang University, Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science and Research Center for Industries of the Future, Westlake University, Institute of Natural Sciences, Westlake Institute for Advanced Study – sequence: 2 givenname: Yuming surname: Pan fullname: Pan, Yuming organization: Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science and Research Center for Industries of the Future, Westlake University, Institute of Natural Sciences, Westlake Institute for Advanced Study – sequence: 3 givenname: Dongshun orcidid: 0009-0006-6914-7416 surname: Ni fullname: Ni, Dongshun email: nidongshun@westlake.edu.cn organization: Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science and Research Center for Industries of the Future, Westlake University, Institute of Natural Sciences, Westlake Institute for Advanced Study – sequence: 4 givenname: Li orcidid: 0000-0003-2233-0222 surname: Deng fullname: Deng, Li email: dengli@westlake.edu.cn organization: Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science and Research Center for Industries of the Future, Westlake University, Institute of Natural Sciences, Westlake Institute for Advanced Study |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39033172$$D View this record in MEDLINE/PubMed |
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| Snippet | Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs)... Abstract Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes... |
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| SubjectTerms | 140/131 140/58 639/638/403/933 639/638/549/884 639/638/549/933 Bicycles Butanes Catalysis Cycloaddition Drug tolerance Ethers Functional groups Hexanes Humanities and Social Sciences Lewis acid multidisciplinary Natural products Octanes Pharmaceutical sciences Prominences Science Science (multidisciplinary) |
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| Title | Facile access to bicyclo[2.1.1]hexanes by Lewis acid-catalyzed formal cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes |
| URI | https://link.springer.com/article/10.1038/s41467-024-50434-6 https://www.ncbi.nlm.nih.gov/pubmed/39033172 https://www.proquest.com/docview/3082862663 https://pubmed.ncbi.nlm.nih.gov/PMC11271461 https://doaj.org/article/ec3fcceb47f346dfaa03631d558b5bba |
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