Gold‐Catalyzed Atroposelective Synthesis of 1, 1′‐Binaphthalene‐2, 3′‐diols. (23rd January 2020)

• Record Type: Journal Article
• Authors: Zhang, Jianwei; Simon, Martin; Golz, Christopher; Alcarazo, Manuel
• Is Part Of: Angewandte Chemie. Volume 132:Number 14(2020)
• Page Start: 5696
• Page End: 5699
• Publication Date: 2020-01-23
• Subjects: Goldkatalyse -- Biaryle -- Kationische Liganden -- Chirale Phosphine -- Enantioselektivität; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201915456
• Languages: English
• ISSNs: 0044-8249

Abstract

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. Abstract : Ferngesteuert : Zwei Methylgruppen, die sich strategisch am Rückgrat der Imidazolium‐Komponente eines Katalysators auf Goldbasis befinden, sind unerlässlich, um die gewünschten Binaphtholverbindungen in bis zu 97 % ee zu liefern.