Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates
The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which sig...
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| Format: | Article |
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American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/117062 https://orcid.org/0000-0001-5418-3082 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826190421413330944 |
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| author | Zhou, Yujing Bandar, Jeffrey Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Zhou, Yujing Bandar, Jeffrey Buchwald, Stephen Leffler |
| author_sort | Zhou, Yujing |
| collection | MIT |
| description | The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner. |
| first_indexed | 2024-09-23T08:40:00Z |
| format | Article |
| id | mit-1721.1/117062 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T08:40:00Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1170622022-09-23T13:43:39Z Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates Zhou, Yujing Bandar, Jeffrey Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Zhou, Yujing Bandar, Jeffrey Buchwald, Stephen Leffler The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner. National Institutes of Health (U.S.) (Grant GM46059) National Institutes of Health (U.S.) (Grant GM058160-17S1) National Institutes of Health (U.S.) (Grant GM112197) 2018-07-24T14:08:22Z 2018-07-24T14:08:22Z 2017-06 2017-05 2018-07-18T17:34:02Z Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/117062 Zhou, Yujing et al. “Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.” Journal of the American Chemical Society 139, 24 (June 2017): 8126–8129 © 2017 American Chemical Society https://orcid.org/0000-0001-5418-3082 https://orcid.org/0000-0003-3875-4775 http://dx.doi.org/10.1021/JACS.7B04937 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Zhou, Yujing Bandar, Jeffrey Buchwald, Stephen Leffler Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title | Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title_full | Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title_fullStr | Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title_full_unstemmed | Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title_short | Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates |
| title_sort | enantioselective cuh catalyzed hydroacylation employing unsaturated carboxylic acids as aldehyde surrogates |
| url | http://hdl.handle.net/1721.1/117062 https://orcid.org/0000-0001-5418-3082 https://orcid.org/0000-0003-3875-4775 |
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