Asymmetric cross-aldol reactions of α-keto hydrazones and α,β-unsaturated γ-keto hydrazones with trifluoromethyl ketones†
Saúl
Alberca, 
a
Esteban
Matador,
a
Ma
de Gracia Retamosa,
*ab
Rosario
Fernández,
*a
José M.
Lassaletta
*c
and
David
Monge
*a
a
Esteban
Matador,
a
Ma
de Gracia Retamosa,
*ab
Rosario
Fernández,
*a
José M.
Lassaletta
*c
and
David
Monge
*a
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.
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