Palladium-Catalyzed Divergent Enantioselective Functionalization of Cyclobutenes
Aliphatic strained rings have been increasingly applied in medicinal chemistry due to their beneficial physicochemical and pharmacokinetic properties. However, the divergent synthesis of enantioenriched cyclobutane derivatives with various structural patterns continues to be a significant challenge....
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| Published in | Journal of the American Chemical Society Vol. 146; no. 18; pp. 12691 - 12701 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
08.05.2024
Amer Chemical Soc |
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| Online Access | Get full text |
| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/jacs.4c02215 |
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| Abstract | Aliphatic strained rings have been increasingly applied in medicinal chemistry due to their beneficial physicochemical and pharmacokinetic properties. However, the divergent synthesis of enantioenriched cyclobutane derivatives with various structural patterns continues to be a significant challenge. Here, we disclose a palladium-catalyzed enantioselective desymmetrization of cyclobutenes, resulting in a series of hydroarylation and 1,2- and 1,3-diarylation products via the interceptions of a common Heck intermediate. Mechanistic investigations provide valuable insights into understanding the catalytic mode of the palladium catalysts and the observed variations in the deuterium-responsive behavior during reactions. Furthermore, the synthetic utility is demonstrated in the syntheses of deuterated drug candidate belaperidone skeletons and pseudosymmetrical truxinic acid-type derivatives. |
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| AbstractList | Aliphatic strained rings have been increasingly applied in medicinal chemistry due to their beneficial physicochemical and pharmacokinetic properties. However, the divergent synthesis of enantioenriched cyclobutane derivatives with various structural patterns continues to be a significant challenge. Here, we disclose a palladium-catalyzed enantioselective desymmetrization of cyclobutenes, resulting in a series of hydroarylation and 1,2- and 1,3-diarylation products via the interceptions of a common Heck intermediate. Mechanistic investigations provide valuable insights into understanding the catalytic mode of the palladium catalysts and the observed variations in the deuterium-responsive behavior during reactions. Furthermore, the synthetic utility is demonstrated in the syntheses of deuterated drug candidate belaperidone skeletons and pseudosymmetrical truxinic acid-type derivatives. Aliphatic strained rings have been increasingly applied in medicinal chemistry due to their beneficial physicochemical and pharmacokinetic properties. However, the divergent synthesis of enantioenriched cyclobutane derivatives with various structural patterns continues to be a significant challenge. Here, we disclose a palladium-catalyzed enantioselective desymmetrization of cyclobutenes, resulting in a series of hydroarylation and 1,2- and 1,3-diarylation products via the interceptions of a common Heck intermediate. Mechanistic investigations provide valuable insights into understanding the catalytic mode of the palladium catalysts and the observed variations in the deuterium-responsive behavior during reactions. Furthermore, the synthetic utility is demonstrated in the syntheses of deuterated drug candidate belaperidone skeletons and pseudosymmetrical truxinic acid-type derivatives.Aliphatic strained rings have been increasingly applied in medicinal chemistry due to their beneficial physicochemical and pharmacokinetic properties. However, the divergent synthesis of enantioenriched cyclobutane derivatives with various structural patterns continues to be a significant challenge. Here, we disclose a palladium-catalyzed enantioselective desymmetrization of cyclobutenes, resulting in a series of hydroarylation and 1,2- and 1,3-diarylation products via the interceptions of a common Heck intermediate. Mechanistic investigations provide valuable insights into understanding the catalytic mode of the palladium catalysts and the observed variations in the deuterium-responsive behavior during reactions. Furthermore, the synthetic utility is demonstrated in the syntheses of deuterated drug candidate belaperidone skeletons and pseudosymmetrical truxinic acid-type derivatives. |
| Author | Wang, Minyan Wang, Zhonggui Zhu, Jie Lu, Ping |
| AuthorAffiliation | Research Center for Molecular Recognition and Synthesis, Department of Chemistry State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering |
| AuthorAffiliation_xml | – name: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering – name: Research Center for Molecular Recognition and Synthesis, Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Zhonggui surname: Wang fullname: Wang, Zhonggui organization: Research Center for Molecular Recognition and Synthesis, Department of Chemistry – sequence: 2 givenname: Jie surname: Zhu fullname: Zhu, Jie organization: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering – sequence: 3 givenname: Minyan orcidid: 0000-0003-3896-5986 surname: Wang fullname: Wang, Minyan email: wangmy@nju.edu.cn organization: State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering – sequence: 4 givenname: Ping orcidid: 0000-0002-2259-2700 surname: Lu fullname: Lu, Ping email: plu@fudan.edu.cn organization: Research Center for Molecular Recognition and Synthesis, Department of Chemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38676653$$D View this record in MEDLINE/PubMed |
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| Keywords | ALKENES DIARYLATION |
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| Title | Palladium-Catalyzed Divergent Enantioselective Functionalization of Cyclobutenes |
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