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Asymmetric synthesis of 2-substituted Azetidin-3-ones via metalated SAMP/RAMP hydrazones
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Pancholi, Alpa K., Geden, Joanna V., Clarkson, Guy J. and Shipman, Michael (2016) Asymmetric synthesis of 2-substituted Azetidin-3-ones via metalated SAMP/RAMP hydrazones. Journal of Organic Chemistry, 81 (17). pp. 7984-7992. doi:10.1021/acs.joc.6b01284
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Official URL: http://dx.doi.org/10.1021/acs.joc.6b01284
Abstract
2-Substituted azetidin-3-ones can be prepared in good yields and enantioselectivities (up to 85% ee) by a one-pot procedure involving the metalation of the SAMP/RAMP hydrazones of N-Boc-azetidin-3-one, reaction with a wide range of electrophiles, including alkyl, allyl and benzyl halides and carbonyl compounds, followed by hydrolysis using oxalic acid.
| Item Type: | Journal Article | ||||||||||
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| Subjects: | R Medicine > RM Therapeutics. Pharmacology | ||||||||||
| Divisions: | Faculty of Science > Chemistry | ||||||||||
| Library of Congress Subject Headings (LCSH): | Drug development | ||||||||||
| Journal or Publication Title: | Journal of Organic Chemistry | ||||||||||
| Publisher: | American Chemical Society | ||||||||||
| ISSN: | 0022-3263 | ||||||||||
| Official Date: | 2 September 2016 | ||||||||||
| Dates: |
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| Volume: | 81 | ||||||||||
| Number: | 17 | ||||||||||
| Page Range: | pp. 7984-7992 | ||||||||||
| DOI: | 10.1021/acs.joc.6b01284 | ||||||||||
| Status: | Peer Reviewed | ||||||||||
| Publication Status: | Published | ||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||
| Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick |
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