Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes
A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society
2011
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| Online Access: | http://hdl.handle.net/1721.1/67692 |
| _version_ | 1826206940463628288 |
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| author | Smith, Sean W. Fu, Gregory C. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Smith, Sean W. Fu, Gregory C. |
| author_sort | Smith, Sean W. |
| collection | MIT |
| description | A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds. |
| first_indexed | 2024-09-23T13:41:16Z |
| format | Article |
| id | mit-1721.1/67692 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:41:16Z |
| publishDate | 2011 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | mit-1721.1/676922022-09-28T15:30:05Z Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes Smith, Sean W. Fu, Gregory C. Massachusetts Institute of Technology. Department of Chemistry Fu, Gregory C. Smith, Sean W. Fu, Gregory C. A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds. National Institutes of Health (U.S.) (National Institute of General Medical Sciences, Grant R01-GM57034) Merck Research Laboratories Novartis (Firm) 2011-12-15T14:35:50Z 2011-12-15T14:35:50Z 2009-09 Article http://purl.org/eprint/type/JournalArticle http://hdl.handle.net/1721.1/67692 Smith, Sean W., and Gregory C. Fu. “Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes.” Journal of the American Chemical Society 131.40 (2009): 14231-14233. en_US http://dx.doi.org/10.1021/ja9061823 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 Prof. Fu via Diane Johansen |
| spellingShingle | Smith, Sean W. Fu, Gregory C. Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title | Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title_full | Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title_fullStr | Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title_full_unstemmed | Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title_short | Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes |
| title_sort | asymmetric carbon carbon bond formation gamma to a carbonyl group phosphine catalyzed addition of nitromethane to allenes |
| url | http://hdl.handle.net/1721.1/67692 |
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