Collect. Czech. Chem. Commun. 2003, 68, 907-916

Synthesis of 2-Hydroxy-8'-(hydroxymethyl)-1,1'-binaphthalene (iso-Homo-BINOL). A New Structural Pattern in the Binaphthyl Realm

Štěpán Vyskočila,b,*, Stephen C. Lockhartb, William L. Mitchellc and Pavel Kočovskýb,*

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K.
c Department of Chemistry, GlaxoSmithKline PLC, The Frythe, Welwyn, Herts. AL6 9AR, U.K.


The title compound 7 has been synthesized in a racemic form, using Suzuki coupling (8 + 1516) as the key step. Pure enantiomer (S)-(-)-7 has been obtained by carbonylation of the known bromide (S)-(+)-12 followed by reduction of the resulting methyl ester (S)-(+)-18 with LiAlH4.

Keywords: Biaryls; Binaphthyls; Axially chiral ligands; Alcohols; Phenols; Suzuki-Miyaura cross-coupling; NOBIN; Asymmetric reductions.

References: 50 live references.