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Bifunctional Squaramide Organocatalysts for the Asymmetric Addition of Formaldehyde tert‐ Butylhydrazone to Simple Aldehydes
Author(s) -
Matador Esteban,
de Gracia Retamosa María,
Monge David,
IglesiasSigüenza Javier,
Fernández Rosario,
Lassaletta José M.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801052
Subject(s) - squaramide , bifunctional , chemistry , amide , organocatalysis , regioselectivity , reactivity (psychology) , organic chemistry , nucleophile , formaldehyde , derivatization , hemiaminal , amination , catalysis , enantioselective synthesis , high performance liquid chromatography , medicine , alternative medicine , pathology
The 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.