Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

Smith, Andrew David; Davies, Alyn; Slawin, Alexandra Martha Zoya

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dc.contributor.author	Smith, Andrew David
dc.contributor.author	Davies, Alyn
dc.contributor.author	Slawin, Alexandra Martha Zoya
dc.date.accessioned	2016-10-26T23:34:08Z
dc.date.available	2016-10-26T23:34:08Z
dc.date.issued	2015-12-14
dc.identifier.citation	Smith , A D , Davies , A & Slawin , A M Z 2015 , ' Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes ' , Chemistry - A European Journal , vol. 21 , no. 52 , pp. 18944–18948 . https://doi.org/10.1002/chem.201504256	en
dc.identifier.issn	0947-6539
dc.identifier.other	PURE: 228175618
dc.identifier.other	PURE UUID: eb991379-ddbc-41cc-8620-3255a2c30836
dc.identifier.other	Scopus: 84955192735
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/36567493
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/56861621
dc.identifier.other	WOS: 000368282100011
dc.identifier.uri	https://hdl.handle.net/10023/9709
dc.description	The authors thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.).	en
dc.description.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.
dc.language.iso	eng
dc.relation.ispartof	Chemistry - A European Journal	en
dc.rights	© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1002/chem.201504256	en
dc.subject	Organocatalysis	en
dc.subject	Lewis-base	en
dc.subject	N-heterocyclic carbene	en
dc.subject	Pentafluoroethyl	en
dc.subject	Oxetane	en
dc.subject	QD Chemistry	en
dc.subject	NDAS	en
dc.subject.lcc	QD	en
dc.title	Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes	en
dc.type	Journal article	en
dc.contributor.sponsor	EPSRC	en
dc.description.version	Postprint	en
dc.contributor.institution	University of St Andrews. School of Chemistry	en
dc.contributor.institution	University of St Andrews. Biomedical Sciences Research Complex	en
dc.contributor.institution	University of St Andrews. EaSTCHEM	en
dc.identifier.doi	https://doi.org/10.1002/chem.201504256
dc.description.status	Peer reviewed	en
dc.date.embargoedUntil	2016-10-26
dc.identifier.url	http://onlinelibrary.wiley.com/doi/10.1002/chem.201504256/abstract#footer-support-info	en
dc.identifier.grantnumber	EP/K039210/1	en

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