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Bifunctional Squaramide Organocatalysts for the Asymmetric Addition of Formaldehyde tert-Butylhydrazone to Simple Aldehydes

AuthorsMatador, Esteban; Retamosa Hernández, María Gracia; Monge, David; Iglesias-Sigüenza, Javier; Fernández, Rosario; Lassaletta, José M.
Issue Date2018
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 24: 6854- 6860 (2018)
AbstractThe nucleophilic addition of formaldehyde tert-butylhydrazone to simple aldehydes (a formal hetero-carbonyl–ene reaction) can be performed with good reactivity and excellent enantioselectivity by virtue of the dual hydrogen-bonding activation exerted by amide–squaramide organocatalysts. The resulting hydroxydiazenes (azo alcohols) were isolated in high yields as enantiomerically enriched azoxy compounds after a regioselective azo-to-azoxy transformation. Subsequent derivatization provides an entry to relevant amino alcohols, oxazolidinones, and derivatives thereof.
Identifiersdoi: 10.1002/chem.201801052
issn: 1521-3765
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