Asymmetric organocatalyzed phospha-michael addition for the direct synthesis of biologically active chromenylphosphonates

Marqués-López, Eugenia (Universidad de Zaragoza) ; Gimeno Sonsona, Isaac ; Garcés-Marín, Miryam ; Gimeno, M. Concepción ; Pérez Herrera, Raquel

Resumen: The potential of phosphites as nucleophiles for the asymmetric synthesis of chiral chromene derivatives has been overlooked in the literature. Herein, we report a promising approach via asymmetric organocatalyzed phospha‐Michael addition to iminochromenes, using a bifunctional squaramide, which gives access to chromenylphosphonates, an interesting family of bioactive compounds. Our optimized protocol provides very good reactivity, affording yields of up to 95% and with chiral products exhibiting an enantiomeric excess of up to 98%.

Idioma: Inglés

DOI: 10.1002/adsc.202300563

Año: 2023

Publicado en: Advanced Synthesis and Catalysis 365, 19 (2023), 3234-3240
ISSN: 1615-4150

Factor impacto JCR: 4.4 (2023)

Categ. JCR: CHEMISTRY, ORGANIC rank: 8 / 58 = 0.138 (2023) - Q1 - T1
Categ. JCR: CHEMISTRY, APPLIED rank: 19 / 74 = 0.257 (2023) - Q2 - T1

Factor impacto CITESCORE: 9.4 - Organic Chemistry (Q1) - Catalysis (Q2)

Factor impacto SCIMAGO: 1.02 - Organic Chemistry (Q1) - Catalysis (Q2)

Financiación: info:eu-repo/grantAgreement/ES/AEI/PID2019-104379RB-C21
Financiación: info:eu-repo/grantAgreement/ES/AEI/PID2020-117455GB-I00
Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-23R

Tipo y forma: Article (Published version)

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