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Formaldehyde tert-butyl hydrazone as a formyl anion equivalent: asymmetric addition to carbonyl compounds.
Matador, Esteban; de Gracia Retamosa, María; Monge, David; Fernández, Rosario; Lassaletta, José M.
Affiliation
  • Matador E; Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación Avanzada (ORFEO-CINQA), C/Prof. García González, 1, 41012 Sevilla, Spain. dmonge@us.es ffernan@us.es.
Chem Commun (Camb) ; 56(65): 9256-9267, 2020 Aug 21.
Article in En | MEDLINE | ID: mdl-32626864
The asymmetric 1,2-addition of formyl anion equivalents to carbonyl compounds is a powerful synthetic tool that ideally provide access to highly functionalizable α-hydroxy aldehydes in an enantioselective fashion. In this context, the nucleophilic character of formaldehyde hydrazones, together with their remarkable stability as monomeric species, has been exploited for the functionalization of diverse carbonyl compounds, using initially auxiliary-based methodologies and, more recently, catalytic enantioselective versions. This feature article highlights our research progress employing formaldehyde tert-butyl hydrazone as a versatile formyl anion equivalent, in combination with bifunctional H-bonding organocatalysis. The design and optimization of different catalytic systems, focusing on a dual activation of both reagents, is reviewed, as well as the racemization free unmasking of the formyl group and representative product transformations for the construction of valuable, densely functionalyzed chiral building blocks.

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2020 Document type: Article Country of publication:

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2020 Document type: Article Country of publication: