Barta, Katalin published the artcileA new class of 3′-sulfonyl BINAPHOS ligands: modulation of activity and selectivity in asymmetric palladium-catalysed hydrophosphorylation of styrene, HPLC of Formula: 126613-06-7, the publication is Advanced Synthesis & Catalysis (2008), 350(13), 2013-2023, database is CAplus.
Pd-catalyzed mono-phosphorylation of (R)-2,2′-bisperfluoroalkanesulfonates of BINOL (RF = CF3 or C4F9) by a diaryl phosphinate [Ar2P(O)H] followed by phosphine oxide reduction (Cl3SiH) then Li diisopropylamide-mediated anionic thia-Fries rearrangement furnishes enantiomerically-pure (R)-2′-diarylphosphino-2′-hydroxy-3′-perfluoralkanesulfonyl-1,1′-binaphthalenes [(R)-8ab and (R)-8g–j], which can be further diversified by Grignard reagent (RMgX)-mediated CF3-displacement [→(R)-8c–f]. Coupling of (R)-8a–j with (S)-1,1′-binaphthalene-2,2′-dioxychlorophosphine (S)-9 generates 3′-sulfonyl BINAPHOS ligands (R,S)-10a–j in good yields (43-82%). These new ligands are of utility in the asym. hydrophosphonylation of styrene by 4,4,5,5-tetramethyl-1,3,2-dioxaphospholane 2-oxide, for which a combination of the chiral ligands with either [Pd(Cp)(allyl)] or [Pd(allyl)(MeCN)2]+/NaCH(CO2Me)2 proves to be a convenient and active pre-catalyst system. A combination of an electron-rich phosphine moiety and an electron-deficient 3′-sulfone moiety provides the best enantioselectivity to date for this process, affording the branched 2-phenethenephosphonate, (-)-iso-3, in up to 74% ee with ligand (R,S)-10i, where Ar = p-anisyl and the 3′-SO2R group is triflone.
Advanced Synthesis & Catalysis published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, HPLC of Formula: 126613-06-7.
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https://en.wikipedia.org/wiki/Ester,
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