A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence
A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner–Wadsworth–Emmons olefination, thus converting a three-operation procedure into a single, uninter...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/76285 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826205853836902400 |
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| author | Webb, Damien Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Webb, Damien Jamison, Timothy F. |
| author_sort | Webb, Damien |
| collection | MIT |
| description | A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner–Wadsworth–Emmons olefination, thus converting a three-operation procedure into a single, uninterrupted system that eliminates the need for isolation or purification of the aldehyde intermediates. The homologated products are obtained in high yield and selectivity. |
| first_indexed | 2024-09-23T13:20:26Z |
| format | Article |
| id | mit-1721.1/76285 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:20:26Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/762852022-10-01T14:37:06Z A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence Webb, Damien Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F. Webb, Damien Jamison, Timothy F. A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner–Wadsworth–Emmons olefination, thus converting a three-operation procedure into a single, uninterrupted system that eliminates the need for isolation or purification of the aldehyde intermediates. The homologated products are obtained in high yield and selectivity. Novartis-MIT Center for Continuous Manufacturing 2013-01-17T18:18:32Z 2013-01-17T18:18:32Z 2012-04 2012-03 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/76285 Webb, Damien, and Timothy F. Jamison. “A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence.” Organic Letters 14.10 (2012): 2465–2467. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/ol300722e Organic Letters 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) Prof. Jamison via Erja Kajosalo |
| spellingShingle | Webb, Damien Jamison, Timothy F. A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title | A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title_full | A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title_fullStr | A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title_full_unstemmed | A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title_short | A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence |
| title_sort | continuous homologation of esters an efficient telescoped reduction olefination sequence |
| url | http://hdl.handle.net/1721.1/76285 https://orcid.org/0000-0002-8601-7799 |
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