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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

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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
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:
DateEvent
2 September 2016Published
22 July 2016Available
22 July 2016Accepted
30 May 2016Submitted
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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