Enantioselective Hydrocarbamoylation of Alkenes
The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an alternative, an enantioselective hydrocarbamoylation of alken...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Wiley
2022
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| Online Access: | https://hdl.handle.net/1721.1/145709 |
| _version_ | 1826192225409695744 |
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| author | Feng, Sheng Dong, Yuyang Buchwald, Stephen L |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Feng, Sheng Dong, Yuyang Buchwald, Stephen L |
| author_sort | Feng, Sheng |
| collection | MIT |
| description | The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an alternative, an enantioselective hydrocarbamoylation of alkenes leveraging dual copper hydride and palladium catalysis to enable the use of readily available carbamoyl chlorides as a practical carbamoylating reagent. The protocol is applicable to various types of olefins, including alkenyl arenes, terminal alkenes, and 1,1-disubstituted alkenes. Substrates containing a diverse range of functional groups as well as heterocyclic substructures undergo functionalization to provide α- and β-chiral amides in good yields and with excellent enantioselectivities. |
| first_indexed | 2024-09-23T09:07:49Z |
| format | Article |
| id | mit-1721.1/145709 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T09:07:49Z |
| publishDate | 2022 |
| publisher | Wiley |
| record_format | dspace |
| spelling | mit-1721.1/1457092022-10-07T03:42:05Z Enantioselective Hydrocarbamoylation of Alkenes Feng, Sheng Dong, Yuyang Buchwald, Stephen L Massachusetts Institute of Technology. Department of Chemistry The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an alternative, an enantioselective hydrocarbamoylation of alkenes leveraging dual copper hydride and palladium catalysis to enable the use of readily available carbamoyl chlorides as a practical carbamoylating reagent. The protocol is applicable to various types of olefins, including alkenyl arenes, terminal alkenes, and 1,1-disubstituted alkenes. Substrates containing a diverse range of functional groups as well as heterocyclic substructures undergo functionalization to provide α- and β-chiral amides in good yields and with excellent enantioselectivities. 2022-10-06T15:09:01Z 2022-10-06T15:09:01Z 2022-08 2022-10-06T15:01:03Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/145709 Feng, Sheng, Dong, Yuyang and Buchwald, Stephen L. 2022. "Enantioselective Hydrocarbamoylation of Alkenes." Angewandte Chemie International Edition, 61 (31). en 10.1002/anie.202206692 Angewandte Chemie International Edition Creative Commons Attribution-NonCommercial-NoDerivs License http://creativecommons.org/licenses/by-nc-nd/4.0/ application/pdf Wiley Wiley |
| spellingShingle | Feng, Sheng Dong, Yuyang Buchwald, Stephen L Enantioselective Hydrocarbamoylation of Alkenes |
| title | Enantioselective Hydrocarbamoylation of Alkenes |
| title_full | Enantioselective Hydrocarbamoylation of Alkenes |
| title_fullStr | Enantioselective Hydrocarbamoylation of Alkenes |
| title_full_unstemmed | Enantioselective Hydrocarbamoylation of Alkenes |
| title_short | Enantioselective Hydrocarbamoylation of Alkenes |
| title_sort | enantioselective hydrocarbamoylation of alkenes |
| url | https://hdl.handle.net/1721.1/145709 |
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