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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

Simon M. Nicolle

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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