Simon M. Nicolle
C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
Nicolle, Simon M.; Nortcliffe, Andrew; Bartrum, Hannah E.; Lewis, William; Hayes, Christopher J.; Moody, Christopher J.
Authors
ANDREW NORTCLIFFE Andrew.Nortcliffe@nottingham.ac.uk
Associate Professor
Hannah E. Bartrum
William Lewis
CHRIS HAYES chris.hayes@nottingham.ac.uk
Professor of Organic Chemistry
Christopher J. Moody
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.
Citation
Nicolle, S. M., Nortcliffe, A., Bartrum, H. E., Lewis, W., Hayes, C. J., & Moody, C. J. (in press). C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery. Chemistry - A European Journal, https://doi.org/10.1002/chem.201703746
Journal Article Type | Article |
---|---|
Acceptance Date | Aug 10, 2017 |
Online Publication Date | Sep 5, 2017 |
Deposit Date | Sep 8, 2017 |
Publicly Available Date | Mar 29, 2024 |
Journal | Wiley online library |
Print ISSN | 0947-6539 |
Electronic ISSN | 1521-3765 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
DOI | https://doi.org/10.1002/chem.201703746 |
Keywords | C?H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds |
Public URL | https://nottingham-repository.worktribe.com/output/880914 |
Publisher URL | http://onlinelibrary.wiley.com/doi/10.1002/chem.201703746/full |
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. |
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