Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols

Jianwei Zhang, Martín Simón, Christopher Golz, Manuel Alcarazo

Angewandte Chemie International Edition · 2019 · 73 citations · 29 references

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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 α-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.

References

29