Asymmetric Organocatalyzed Phospha‐Michael Addition for the Direct Synthesis of Biologically Active Chromenylphosphonates
Eugenia Marqués‐López, Isaac G. Sonsona, Miryam Garcés‐Marín, M. Concepción Gimeno, Raquel P. Herrera
Abstract
Abstract 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%.
Topics & Concepts
SquaramideChemistryBifunctionalMichael reactionEnantioselective synthesisNucleophileOrganocatalysisEnantiomerEnantiomeric excessReactivity (psychology)Combinatorial chemistryOptically activeOrganic chemistryCatalysisAlternative medicinePathologyMedicineAsymmetric Synthesis and CatalysisCarbohydrate Chemistry and SynthesisSynthetic Organic Chemistry Methods