Stereospecific Asymmetric N‑Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights
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https://figshare.com/articles/dataset/Stereospecific_Asymmetric_N_Heterocyclic_Carbene_NHC_Catalyzed_Redox_Synthesis_of_Trifluoromethyl_Dihydropyranones_and_Mechanistic_Insights/2374753
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资源简介：
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.
创建时间：
2013-09-20
