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Asymmetric synthesis of 2-substituted Azetidin-3-ones via metalated SAMP/RAMP hydrazones
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Pancholi, Alpa, 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 . doi:10.1021/acs.joc.6b01284 (In Press)
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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: | 22 July 2016 | ||||||||
| Dates: |
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| DOI: | 10.1021/acs.joc.6b01284 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | In Press | ||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||
| Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick |
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