Phosphonation of 1, 1′-binaphthalene-2, 2′-diol (BINOL): synthesis of (R)-and (S)-2, 2′-dihydroxy-1, 1′-binaphthalene-6, 6′-diyldiphosphonic acid

PA Jaffrès, N Bar, D Villemin

Index: Jaffres, Paul-Alain; Bar, Nathalie; Villemin, Didier Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 13 p. 2083 - 2089

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Citation Number: 22

Abstract

The synthesis of 6, 6′-bis (diethoxyphosphoryl)-1, 1′-binaphthalene-2, 2′-diol 1 in racemic and chiral forms is described. This synthesis, which involves a palladium-assisted phosphonation step, allows study of the phosphonation of bromophenol as an electron-rich aryl bromide model. Furthermore, the synthesis of 2, 2′-dihydroxy-1, 1′-binaphthalene-6, 6′-diyldiphosphonic acid 2, from its diester 1, leads to a key intermediate in the synthesis ...