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Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals
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Clark, Andrew J., Filik, Robert P., Thomas, Gerard H. and Sherringham, John (2013) Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals. Tetrahedron Letters, Volume 54 (Number 31). pp. 4094-4097. doi:10.1016/j.tetlet.2013.05.109 ISSN 0040-4039.
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2013.05.109
Abstract
2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
| Journal or Publication Title: | Tetrahedron Letters | ||||
| Publisher: | Elsevier | ||||
| ISSN: | 0040-4039 | ||||
| Official Date: | July 2013 | ||||
| Dates: |
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| Volume: | Volume 54 | ||||
| Number: | Number 31 | ||||
| Page Range: | pp. 4094-4097 | ||||
| DOI: | 10.1016/j.tetlet.2013.05.109 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
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