Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts

Castán, A. ; Badorrey, R. (Universidad de Zaragoza) ; Gálvez, J.A. (Universidad de Zaragoza) ; López-Ram-De-Víu, P. (Universidad de Zaragoza) ; Díaz-De-Villegas, M.D.

Resumen: Novel bifunctional pyrrolidine-based organocatalysts for the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optimal reaction conditions, these bifunctional organocatalysts showed a high catalytic efficiency (almost quantitative yield in most cases) and stereoselectivity in the Michael addition reactions of a variety of aldehydes (up to 98 : 2 dr and 97% ee) and ketones (up to 98 : 2 dr and 99% ee) to nitroolefins.

Idioma: Inglés

DOI: 10.1039/c7ob02798b

Año: 2018

Publicado en: Organic & Biomolecular Chemistry 16, 6 (2018), 924-935
ISSN: 1477-0520

Factor impacto JCR: 3.49 (2018)

Categ. JCR: CHEMISTRY, ORGANIC rank: 14 / 57 = 0.246 (2018) - Q1 - T1

Factor impacto SCIMAGO: 1.119 - Biochemistry (Q1) - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E102

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)