Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes
The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions invol...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/82541 https://orcid.org/0000-0001-5827-3552 |
| _version_ | 1826203107427614720 |
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| author | Ibrahem, Ismail Yu, Miao Hoveyda, Amir H. Schrock, Richard Royce |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Ibrahem, Ismail Yu, Miao Hoveyda, Amir H. Schrock, Richard Royce |
| author_sort | Ibrahem, Ismail |
| collection | MIT |
| description | The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E). |
| first_indexed | 2024-09-23T12:31:45Z |
| format | Article |
| id | mit-1721.1/82541 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:31:45Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
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| spelling | mit-1721.1/825412022-10-01T09:33:16Z Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes Ibrahem, Ismail Yu, Miao Hoveyda, Amir H. Schrock, Richard Royce Massachusetts Institute of Technology. Department of Chemistry Schrock, Richard Royce The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E). National Institutes of Health (U.S.) (Grant GM-59426) National Science Foundation (U.S.) (DBI-0619576) 2013-11-22T14:46:10Z 2013-11-22T14:46:10Z 2009-02 2009-01 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/82541 Ibrahem, Ismail, Miao Yu, Richard R. Schrock, and Amir H. Hoveyda. “Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes.” Journal of the American Chemical Society 131, no. 11 (March 25, 2009): 3844-3845. https://orcid.org/0000-0001-5827-3552 en_US http://dx.doi.org/10.1021/ja900097n 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 | Ibrahem, Ismail Yu, Miao Hoveyda, Amir H. Schrock, Richard Royce Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title_full | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title_fullStr | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title_full_unstemmed | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title_short | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
| title_sort | highly z and enantioselective ring opening cross metathesis reactions catalyzed by stereogenic at mo adamantylimido complexes |
| url | http://hdl.handle.net/1721.1/82541 https://orcid.org/0000-0001-5827-3552 |
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