Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights

Davies, Alyn T., Taylor, James E., Douglas, James, Collett, Christopher J., Morrill, Louis ORCID: https://orcid.org/0000-0002-6453-7531, Fallan, Charlene, Slawin, Alexandra M. Z., Churchill, Gwydion and Smith, Andrew D. 2013. Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights. Journal of Organic Chemistry 78 (18) , pp. 9243-9257. 10.1021/jo401433q

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels–Alder reactions of α-aroyloxyaldehydes with β-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-β-trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	ACS
ISSN:	0022-3263
Last Modified:	28 Oct 2022 09:22
URI:	https://orca.cardiff.ac.uk/id/eprint/74296

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