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

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-oxe...

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Main Authors:	Nicolle, Simon M., Nortcliffe, Andrew, Bartrum, Hannah E., Lewis, William, Hayes, Christopher J., Moody, Christopher J.
Format:	Article
Published:	Wiley 2017
Subjects:	C−H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds
Online Access:	https://eprints.nottingham.ac.uk/45531/

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author	Nicolle, Simon M. Nortcliffe, Andrew Bartrum, Hannah E. Lewis, William Hayes, Christopher J. Moody, Christopher J.
author_facet	Nicolle, Simon M. Nortcliffe, Andrew Bartrum, Hannah E. Lewis, William Hayes, Christopher J. Moody, Christopher J.
author_sort	Nicolle, Simon M.
building	Nottingham Research Data Repository
collection	Online Access
description	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.
first_indexed	2025-11-14T19:59:16Z
format	Article
id	nottingham-45531
institution	University of Nottingham Malaysia Campus
institution_category	Local University
last_indexed	2025-11-14T19:59:16Z
publishDate	2017
publisher	Wiley
recordtype	eprints
repository_type	Digital Repository
spelling	nottingham-455312020-05-04T19:04:30Z https://eprints.nottingham.ac.uk/45531/ 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. 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. Wiley 2017-09-05 Article PeerReviewed Nicolle, Simon M., Nortcliffe, Andrew, Bartrum, Hannah E., Lewis, William, 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 C−H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds http://onlinelibrary.wiley.com/doi/10.1002/chem.201703746/full doi:10.1002/chem.201703746 doi:10.1002/chem.201703746
spellingShingle	C−H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds Nicolle, Simon M. Nortcliffe, Andrew Bartrum, Hannah E. Lewis, William Hayes, Christopher J. Moody, Christopher J. C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title	C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title_full	C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title_fullStr	C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title_full_unstemmed	C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title_short	C–H insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
title_sort	c–h insertion as a key step to spiro-oxetanes, scaffolds for drug discovery
topic	C−H activation; drug discovery; ditrogen heterocycles; oxygen heterocycles; spiro compounds
url	https://eprints.nottingham.ac.uk/45531/ https://eprints.nottingham.ac.uk/45531/ https://eprints.nottingham.ac.uk/45531/

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

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