Asymmetric cross-aldol reactions of α-keto hydrazones and α, β-unsaturated γ-keto hydrazones with trifluoromethyl ketones. Issue 89 (26th October 2021)

• Record Type: Journal Article
• Authors: Alberca, Saúl; Matador, Esteban; Iglesias-Sigüenza, Javier; de Gracia Retamosa, Ma; Fernández, Rosario; Lassaletta, José M.; Monge, David
• Is Part Of: Chemical communications. Volume 57:Issue 89(2021)
• Page Start: 11835
• Page End: 11838
• Publication Date: 2021-10-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc05014a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Asymmetric cross-aldol reactions of α-keto hydrazones and α, β-unsaturated γ-keto hydrazones with trifluoromethyl ketones afford easy-to-functionalize tertiary trifluoromethyl alcohols with high enantioselectivity. 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.