Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Castán, A. ; Badorrey, R. (Universidad de Zaragoza) ; Gálvez, J.A. (Universidad de Zaragoza) ; Díaz de Villegas, M.D.

Resumen: New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

Idioma: Inglés

DOI: 10.3762/bjoc.13.59

Año: 2017

Publicado en: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 13 (2017), 612-619
ISSN: 1860-5397

Factor impacto JCR: 2.33 (2017)

Categ. JCR: CHEMISTRY, ORGANIC rank: 25 / 57 = 0.439 (2017) - Q2 - T2

Factor impacto SCIMAGO: 0.929 - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/GAE-102

Tipo y forma: Article (Published version)

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