One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes
An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)...
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| Format: | Article |
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Wiley-VCH Verlag
2015
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| Online Access: | https://eprints.nottingham.ac.uk/46633/ |
| _version_ | 1848797372824420352 |
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| author | Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William |
| author_facet | Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William |
| author_sort | Burroughs, Laurence |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. |
| first_indexed | 2025-11-14T20:02:50Z |
| format | Article |
| id | nottingham-46633 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:50Z |
| publishDate | 2015 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-466332020-05-04T17:13:55Z https://eprints.nottingham.ac.uk/46633/ One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. Wiley-VCH Verlag 2015-09-01 Article PeerReviewed Burroughs, Laurence, Eccleshare, Lee, Ritchie, John, Kulkarni, Omkar, Lygo, Barry, Woodward, Simon and Lewis, William (2015) One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes. Angewandte Chemie International Edition, 54 (36). pp. 10648-10651. ISSN 1521-3773 aldehydes; annulation; carbocycles; medium-ring compounds; synthetic methods http://onlinelibrary.wiley.com/doi/10.1002/anie.201505347/abstract? doi:10.1002/anie.201505347 doi:10.1002/anie.201505347 |
| spellingShingle | aldehydes; annulation; carbocycles; medium-ring compounds; synthetic methods Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title | One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title_full | One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title_fullStr | One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title_full_unstemmed | One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title_short | One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes |
| title_sort | one-pot cannizzaro cascade synthesis of ortho-fused cycloocta-2,5-dien-1-ones from 2-bromo(hetero)aryl aldehydes |
| topic | aldehydes; annulation; carbocycles; medium-ring compounds; synthetic methods |
| url | https://eprints.nottingham.ac.uk/46633/ https://eprints.nottingham.ac.uk/46633/ https://eprints.nottingham.ac.uk/46633/ |