C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery

Nicolle, Simon M. and Nortcliffe, Andrew and Bartrum, Hannah E. and Lewis, William and Hayes, Christopher J. and Moody, Christopher J. (2017) C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery. Wiley online library . ISSN 1521-3765

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Abstract

A new route to spiro-oxetanes, potential scaffolds for drug discovery, is described. The route is based on the selective 1,4-C–H insertion reactions of metallocarbenes, generated from simple carbonyl precursors in flow or batch mode, to give spiro-β-lactones that are rapidly converted into spiro-oxetanes. The three-dimensional and lead like-properties of spiro-oxetanes is illustrated by the conversion of the 1-oxa-7-azaspiro[3,5]nonane scaffold into a range of functionalized derivatives.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Nicolle, S. M., Nortcliffe, A., Bartrum, H. E., Lewis, W., Hayes, C. J. and Moody, C. J. (2017), C−H Insertion as a Key Step to Spiro-Oxetanes, Scaffolds for Drug Discovery. Chem. Eur. J.. doi:10.1002/chem.201703746 which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/chem.201703746/full This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Keywords: C−H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201703746
Depositing User: Smith, Ruth
Date Deposited: 08 Sep 2017 08:43
Last Modified: 08 Sep 2017 15:09
URI: http://eprints.nottingham.ac.uk/id/eprint/45531

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