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Gold-Catalyzed Atroposelective Synthesis of 1,1'-Binaphthalene-2,3'-diols.

ABSTRACT: A highly atroposelective (up to 97?% ee) Au-catalyzed synthesis of 1,1'-binaphthalene-2,3'-diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto-3-ol unit is the use of TADDOL-derived ?-cationic phosphonites as ancillary ligands. Preliminary results demonstrate that the transformation of the obtained binaphthyls into axially chiral monodentate phosphines is possible without degradation of enantiopurity.

SUBMITTER: Zhang J 

PROVIDER: S-EPMC7155015 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Atroposelective Synthesis of 1,1'-Binaphthalene-2,3'-diols.

Zhang Jianwei J   Simon Martin M   Golz Christopher C   Alcarazo Manuel M  

Angewandte Chemie (International ed. in English) 20200123 14

A highly atroposelective (up to 97 % ee) Au-catalyzed synthesis of 1,1'-binaphthalene-2,3'-diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto-3-ol unit is the use of TADDOL-derived α-cationic phosphonites as ancillary ligands. Preliminary results demonstrate that the transformation of the obtained binaphthyls into axially chiral monodentate phosphines is possible without degradati  ...[more]

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