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Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
Ist Teil von
Chemical science (Cambridge), 2019-04, Vol.10 (15), p.4322-4327
Ort / Verlag
England: Royal Society of Chemistry
Erscheinungsjahr
2019
Quelle
EZB Electronic Journals Library
Beschreibungen/Notizen
A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita-Baylis-Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were generated with excellent to good yields (up to 99%) and high enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction was further investigated by the linear free energy relationship (LFER) analysis. A possible transition state was proposed and furthered verified by theoretical calculations.