Reaction of phosphorylated 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dien-1-ones with 2,2′-[1,3-phenylenebis(oxy)]-di(ethan-1-amine)

Catalytic Enantioselective Synthesis of Aryl–Methyl Organophosphorus Compounds

“…Pudovik et al developed the reaction of phosphorylated methylidene quinones with different alcohol and phenol derivatives. 5 The route for synthesizing α-amino phosphonates with a sterically hindered phenol fragment from phosphorylated quinomethanes and different amines was reported independently by Vagapova et al and Azmukhanova et al 6 The reaction of phosphorylated quinomethanes with different thiols in high yield was reported by Gazizov et al 7 However, notwithstanding these developments, the chemistry of phosphorylated quinomethanes remains limited to racemic variants (Scheme 2A).…”

“…Brown viscous oil (25 mg, 0.0486 mmol, 49% yield). FT-IR (thin film): 3741 (m), 3418 6,134.3,128.4,127.9,127.8,127.7,126.3 (d,J = 7.3 Hz),123.8,123.6,118.9,111.7,110.8,71.2 (d,J = 7.4 Hz),70.8 (d,J = 7.5 Hz),42.2 (d,J = 140.6 Hz),34.5,30.4,24.5 (d,J = 2.8 Hz) 3 Hz),134.5,128.5,128.4,127.6 (d,J = 5.0 Hz),126.3 (d,J = 7.3 Hz),125.3 (d,J = 5.9 Hz),124.9,122.0,118.7,112.5,111.6,76.3 (d,J = 7.7 Hz),75.6 (d,J = 8.0 Hz),42.4 (d,J = 140.8 Hz),34.4,34.2,33. ) for an enantiomerically enriched sample with 97.5:2.5 er. The enantiomeric ratio was determined by HPLC analysis using Daicel Chiralpak IG column (IPA/n-hexane 3:97, 1.0 mL/min, 25 °C, 230 nm, τ major = 9.63 min, τ minor = 12.66 min).…”