Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes
The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen sou...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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Wiley Blackwell
2015
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| Online Access: | http://hdl.handle.net/1721.1/99658 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826211632089399296 |
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| author | Niljianskul, Nootaree Zhu, Shaolin Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Niljianskul, Nootaree Zhu, Shaolin Buchwald, Stephen Leffler |
| author_sort | Niljianskul, Nootaree |
| collection | MIT |
| description | The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source. This hydroamination reaction is compatible with differentially substituted vinylsilanes, thus providing access to amino acid mimics and other valuable chiral organosilicon compounds. |
| first_indexed | 2024-09-23T15:09:03Z |
| format | Article |
| id | mit-1721.1/99658 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T15:09:03Z |
| publishDate | 2015 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/996582022-09-29T13:01:00Z Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes Niljianskul, Nootaree Zhu, Shaolin Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Niljianskul, Nootaree Zhu, Shaolin Buchwald, Stephen Leffler The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source. This hydroamination reaction is compatible with differentially substituted vinylsilanes, thus providing access to amino acid mimics and other valuable chiral organosilicon compounds. National Institutes of Health (U.S.) (Award GM58160) 2015-11-02T19:07:55Z 2015-11-02T19:07:55Z 2014-12 2014-10 Article http://purl.org/eprint/type/JournalArticle 14337851 1521-3773 http://hdl.handle.net/1721.1/99658 Niljianskul, Nootaree, Shaolin Zhu, and Stephen L. Buchwald. “Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes.” Angew. Chem. Int. Ed. 54, no. 5 (December 4, 2014): 1638–1641. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1002/anie.201410326 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Niljianskul, Nootaree Zhu, Shaolin Buchwald, Stephen Leffler Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title | Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title_full | Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title_fullStr | Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title_full_unstemmed | Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title_short | Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes |
| title_sort | enantioselective synthesis of α aminosilanes by copper catalyzed hydroamination of vinylsilanes |
| url | http://hdl.handle.net/1721.1/99658 https://orcid.org/0000-0003-3875-4775 |
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