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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 ISSN 0022-3263.

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Official URL: http://dx.doi.org/10.1021/jo4020485

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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:
DateEvent
23 October 2013Published
14 September 2013Submitted
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
Date of first compliant deposit: 26 December 2015
Date of first compliant Open Access: 26 December 2015
Funder: Engineering and Physical Sciences Research Council (EPSRC), University of Warwick
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