Access toP-stereogenic compoundsviadesymmetrizing enantioselective bromination

Abstract

A novel and efficient desymmetrizing asymmetricortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported. Using this asymmetricortho-bromination strategy, a wide range of chiral bisphenol phosphine oxides and bisphenol phosphinates were obtained with good to excellent yields (up to 92%) and enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction could be scaled up, and the synthetic utility of the desiredP-stereogenic compounds was proved by transformations and application in an asymmetric reaction.