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Asymmetric cross-aldol reactions of α-keto hydrazones and α,β-unsaturated γ-keto hydrazones with trifluoromethyl ketones.

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α-Keto hydrazones and α,β-unsaturated γ-keto hydrazones are suitable pro-nucleophiles for asymmetric cross-aldol reactions with trifluoromethyl ketones via aza-di(tri)enamine-type intermediates. A quinidine-derived primary amine catalyst affords tertiary trifluoromethylated alcohols in good-to-excellent… Click to show full abstract

α-Keto hydrazones and α,β-unsaturated γ-keto hydrazones are suitable pro-nucleophiles for asymmetric cross-aldol reactions with trifluoromethyl ketones via aza-di(tri)enamine-type intermediates. A quinidine-derived primary amine catalyst affords tertiary trifluoromethylated alcohols in good-to-excellent yields and high enantioselectivities. Subsequent transformations of hydrazono moieties yield appealing fluorinated carboxylic acids, 1,4-dicarbonyls and γ-keto acids.

Keywords: asymmetric cross; keto hydrazones; keto; cross aldol; unsaturated keto; hydrazones unsaturated

Journal Title: Chemical communications
Year Published: 2021

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