Synthesis of β-Phosphinolactams from Phosphenes and Imines
Xingyang Fu, Xinyao Li, Jiaxi Xu
Abstract
Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.
Topics & Concepts
ChemistryDiazoPhosphineIntramolecular forceStereoselectivitySteric effectsNucleophileArylPhospheneTransition stateMedicinal chemistryStereochemistryPhotochemistryOrganic chemistryCatalysisAlkylStimulationNeuroscienceTranscranial magnetic stimulationBiologySynthesis of β-Lactam CompoundsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions