Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades
Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic direct...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/82116 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1811092837347885056 |
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| author | Morten, Christopher J. Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Morten, Christopher J. Jamison, Timothy F. |
| author_sort | Morten, Christopher J. |
| collection | MIT |
| description | Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening. |
| first_indexed | 2024-09-23T15:29:29Z |
| format | Article |
| id | mit-1721.1/82116 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T15:29:29Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/821162022-10-02T02:47:13Z Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades Morten, Christopher J. Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Morten, Christopher J. Jamison, Timothy F. Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening. Massachusetts Institute of Technology. Dept. of Chemistry (George Buchi Graduate Fellowship) 2013-11-15T15:12:16Z 2013-11-15T15:12:16Z 2009-04 2009-03 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/82116 Morten, Christopher J., and Timothy F. Jamison. “Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades.” Journal of the American Chemical Society 131, no. 19 (May 20, 2009): 6678-6679. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/ja9025243 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 | Morten, Christopher J. Jamison, Timothy F. Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title | Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title_full | Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title_fullStr | Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title_full_unstemmed | Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title_short | Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades |
| title_sort | water overcomes methyl group directing effects in epoxide opening cascades |
| url | http://hdl.handle.net/1721.1/82116 https://orcid.org/0000-0002-8601-7799 |
| work_keys_str_mv | AT mortenchristopherj waterovercomesmethylgroupdirectingeffectsinepoxideopeningcascades AT jamisontimothyf waterovercomesmethylgroupdirectingeffectsinepoxideopeningcascades |