Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach
The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was ap...
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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/1721.1/113059 https://orcid.org/0000-0001-6414-0908 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1811081876888092672 |
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| author | Wang, Yiming Bruno, Nicholas Charles Placeres, Angel L Zhu, Shaolin Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Wang, Yiming Bruno, Nicholas Charles Placeres, Angel L Zhu, Shaolin Buchwald, Stephen Leffler |
| author_sort | Wang, Yiming |
| collection | MIT |
| description | The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (-)-paroxetine. |
| first_indexed | 2024-09-23T11:53:48Z |
| format | Article |
| id | mit-1721.1/113059 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T11:53:48Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1130592022-09-27T22:41:40Z Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach Wang, Yiming Bruno, Nicholas Charles Placeres, Angel L Zhu, Shaolin Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Wang, Yiming Bruno, Nicholas Charles Placeres, Angel L Zhu, Shaolin Buchwald, Stephen Leffler The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (-)-paroxetine. National Institutes of Health (U.S.) (Award GM46059) National Institutes of Health (U.S.) (Award GM112218) 2018-01-11T14:38:05Z 2018-01-11T14:38:05Z 2015-08 2015-07 2018-01-10T16:28:29Z Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/113059 Wang, Yi-Ming et al. “Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach.” Journal of the American Chemical Society 137, 33 (August 2015): 10524–10527 © 2015 American Chemical Society https://orcid.org/0000-0001-6414-0908 https://orcid.org/0000-0003-3875-4775 http://dx.doi.org/10.1021/JACS.5B07061 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) ACS |
| spellingShingle | Wang, Yiming Bruno, Nicholas Charles Placeres, Angel L Zhu, Shaolin Buchwald, Stephen Leffler Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title | Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title_full | Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title_fullStr | Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title_full_unstemmed | Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title_short | Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach |
| title_sort | enantioselective synthesis of carbo and heterocycles through a cuh catalyzed hydroalkylation approach |
| url | http://hdl.handle.net/1721.1/113059 https://orcid.org/0000-0001-6414-0908 https://orcid.org/0000-0003-3875-4775 |
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