Enantioselective NHC‐Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes |
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| Authors: | Alyn T Davies Prof Alexandra M Z Slawin Prof Andrew D Smith |
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| Institution: | EaStCHEM, School of Chemistry University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST (UK) http://ch‐www.st‐andrews.ac.uk/staff/ads/group/ |
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| Abstract: | The N‐heterocyclic carbene (NHC) catalyzed redox formal 2+2] cycloaddition between α‐aroyloxyaldehydes and perfluoroketones, followed by ring‐opening in situ delivers a variety of perfluorinated β‐hydroxycarbonyl compounds in good yield, and excellent diastereo‐ and enantioselectivity. Through a reductive work‐up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee. |
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| Keywords: | Lewis base N‐heterocyclic carbene organocatalysis oxetane pentafluoroethyl |
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