C-H Insertion as a Key Step to Spiro-Oxetanes, Scaffolds for Drug Discovery
Simon M Nicolle1, Andrew Nortcliffe1, Hannah E Bartrum1
1School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom.
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 are illustrated by the conversion of the 1-oxa-7-azaspiro[3,5]nonane scaffold into a range of functionalized derivatives.
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