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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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:	Date Event 2 September 2016 Published 22 July 2016 Available 22 July 2016 Accepted 30 May 2016 Submitted
Date of first compliant deposit:	25 July 2016
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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