Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 18, Pages 9243-9257Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401433q
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Funding
- Royal Society
- European Research Council under the European Union [279850]
- EPSRC
- AstraZeneca
- European Research Council (ERC) [279850] Funding Source: European Research Council (ERC)
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N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with beta-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)-beta-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.
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