Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes
Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in ex...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2015
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| Online Access: | http://hdl.handle.net/1721.1/99676 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1811076579835510784 |
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| author | Zhu, Shaolin Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Zhu, Shaolin Buchwald, Stephen Leffler |
| author_sort | Zhu, Shaolin |
| collection | MIT |
| description | Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis. |
| first_indexed | 2024-09-23T10:24:26Z |
| format | Article |
| id | mit-1721.1/99676 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T10:24:26Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/996762022-09-30T20:54:29Z Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes Zhu, Shaolin Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Zhu, Shaolin Buchwald, Stephen Leffler Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis. National Institutes of Health (U.S.) (Award GM58160) 2015-11-03T13:12:22Z 2015-11-03T13:12:22Z 2014-10 2014-09 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/99676 Zhu, Shaolin, and Stephen L. Buchwald. “Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes.” Journal of the American Chemical Society 136, no. 45 (November 12, 2014): 15913–15916. © 2014 American Chemical Society https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ja509786v 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 | Zhu, Shaolin Buchwald, Stephen Leffler Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title | Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title_full | Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title_fullStr | Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title_full_unstemmed | Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title_short | Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
| title_sort | enantioselective cuh catalyzed anti markovnikov hydroamination of 1 1 disubstituted alkenes |
| url | http://hdl.handle.net/1721.1/99676 https://orcid.org/0000-0003-3875-4775 |
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