Enantioselective NHC-Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes.
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.
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/
Alyn T
AT
Davies
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/
Alexandra M Z
AM
Slawin
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/. ads10@st-andrews.ac.uk.
Andrew D
AD
Smith
Lewis base; N-heterocyclic carbene; organocatalysis; oxetane; pentafluoroethyl