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Asymmetric synthesis of 2-substituted oxetan-3-ones via metalated SAMP/RAMP hydrazones
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Geden, Joanna V., Beasley, Benjamin, Clarkson, Guy J. and Shipman, Michael (2013) Asymmetric synthesis of 2-substituted oxetan-3-ones via metalated SAMP/RAMP hydrazones. The Journal of Organic Chemistry, Volume78 (Number 23). pp. 12243-12250. doi:10.1021/jo4020485
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Official URL: http://dx.doi.org/10.1021/jo4020485
Abstract
2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% ee) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, allyl, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86–90%) by repetition of this lithiation/alkylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.
| Item Type: | Journal Article | ||||||
|---|---|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||
| Library of Congress Subject Headings (LCSH): | Asymmetric synthesis, Hydrazones | ||||||
| Journal or Publication Title: | The Journal of Organic Chemistry | ||||||
| Publisher: | American Chemical Society | ||||||
| ISSN: | 0022-3263 | ||||||
| Official Date: | 23 October 2013 | ||||||
| Dates: |
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| Volume: | Volume78 | ||||||
| Number: | Number 23 | ||||||
| Page Range: | pp. 12243-12250 | ||||||
| DOI: | 10.1021/jo4020485 | ||||||
| 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 | ||||||
| Adapted As: |
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