Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes
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.
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
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
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.).Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.