Enantioselective NHC‐Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes

Autor:	Andrew D. Smith, Alexandra M. Z. Slawin, Alyn Davies
Přispěvatelé:	EPSRC, University of St Andrews. School of Chemistry, University of St Andrews. Biomedical Sciences Research Complex, University of St Andrews. EaSTCHEM
Rok vydání:	2015
Předmět:	Pentafluoroethyl Organocatalysis Organic Chemistry NDAS Enantioselective synthesis General Chemistry QD Chemistry Oxetane Redox Catalysis Cycloaddition chemistry.chemical_compound chemistry Lewis-base Organic chemistry QD Lewis acids and bases N-heterocyclic carbene Carbene
Zdroj:	Chemistry – A European Journal. 21:18944-18948
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201504256
Popis:	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.). 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. Postprint
Databáze:	OpenAIRE
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