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Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides

Qingyu Tian, Jin Ge, Yaopeng Liu, Xi Wu, Zhenghao Li, Guolin Cheng

2024Organic Letters9 citationsDOI

Abstract

The enantioselective synthesis of P(V)-stereogenic compounds has emerged as an interesting research topic primarily due to their significant biological activity and broad application prospects. Herein, we disclose a method for the construction of P(V)-stereogenic compounds from prochiral phosphinamides and aryl iodides via palladium- and chiral norbornene-catalyzed desymmetric annulation. The P(V)-stereogenic compounds were formed with a broad scope with excellent enantiomeric excesses. It is noteworthy that the synthetic value of this procedure was proven by a variety of transition metal-catalyzed cross-coupling reactions using the C-Br bond on the product as a versatile linchpin electrophile.

Topics & Concepts

StereocenterEnantioselective synthesisChemistryAnnulationPalladiumArylNorborneneElectrophileStereochemistryCatalysisEnantiomerCombinatorial chemistryOrganic chemistryAlkylPolymerMonomerCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis
Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides | Litcius