CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers
We report a method to prepare α-chiral carboxylic acid derivatives, including those bearing all-carbon quaternary centers, through an enantioselective CuH-catalyzed hydrocarboxylation of allenes with a commercially available fluoroformate. A broad range of heterocycles and functional groups on the a...
| Príomhchruthaitheoirí: | , |
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| Formáid: | Alt |
| Teanga: | English |
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American Chemical Society (ACS)
2022
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| Rochtain ar líne: | https://hdl.handle.net/1721.1/142063 |
| _version_ | 1826200102237110272 |
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| author | Feng, Sheng Buchwald, Stephen L |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Feng, Sheng Buchwald, Stephen L |
| author_sort | Feng, Sheng |
| collection | MIT |
| description | We report a method to prepare α-chiral carboxylic acid derivatives, including those bearing all-carbon quaternary centers, through an enantioselective CuH-catalyzed hydrocarboxylation of allenes with a commercially available fluoroformate. A broad range of heterocycles and functional groups on the allenes were tolerated in this protocol, giving enantioenriched α-quaternary and tertiary carboxylic acid derivatives in good yields with exclusive branched regioselectivity. The synthetic utility of this approach was further demonstrated by derivatization of the products to afford biologically important compounds, including the antiplatelet drug indobufen. |
| first_indexed | 2024-09-23T11:31:13Z |
| format | Article |
| id | mit-1721.1/142063 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:31:13Z |
| publishDate | 2022 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1420632023-02-10T19:09:33Z CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers Feng, Sheng Buchwald, Stephen L Massachusetts Institute of Technology. Department of Chemistry Massachusetts Institute of Technology. Department of Chemistry We report a method to prepare α-chiral carboxylic acid derivatives, including those bearing all-carbon quaternary centers, through an enantioselective CuH-catalyzed hydrocarboxylation of allenes with a commercially available fluoroformate. A broad range of heterocycles and functional groups on the allenes were tolerated in this protocol, giving enantioenriched α-quaternary and tertiary carboxylic acid derivatives in good yields with exclusive branched regioselectivity. The synthetic utility of this approach was further demonstrated by derivatization of the products to afford biologically important compounds, including the antiplatelet drug indobufen. 2022-04-25T17:37:37Z 2022-04-25T17:37:37Z 2021 2022-04-25T17:28:44Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/142063 Feng, Sheng and Buchwald, Stephen L. 2021. "CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers." Journal of the American Chemical Society, 143 (13). en 10.1021/JACS.1C01880 Journal of the American Chemical Society Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Feng, Sheng Buchwald, Stephen L CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title | CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title_full | CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title_fullStr | CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title_full_unstemmed | CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title_short | CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers |
| title_sort | cuh catalyzed regio and enantioselective hydrocarboxylation of allenes toward carboxylic acids with acyclic quaternary centers |
| url | https://hdl.handle.net/1721.1/142063 |
| work_keys_str_mv | AT fengsheng cuhcatalyzedregioandenantioselectivehydrocarboxylationofallenestowardcarboxylicacidswithacyclicquaternarycenters AT buchwaldstephenl cuhcatalyzedregioandenantioselectivehydrocarboxylationofallenestowardcarboxylicacidswithacyclicquaternarycenters |