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Development of Pharmaceutical Chiral Advanced Intermediates: 2-naphthol with REACH
10 Apr 2019
1,1′-Bi-2-naphthol (BINOL) is an organic compound that is often used as a ligand for transition-metal catalysed asymmetric synthesis. BINOL has axial chirality and the two enantiomers can be readily separated and are stable toward racemisation. The specific rotation of the two enantiomers is ±35.5° (c = 1 in THF). BINOL is a precursor for another chiral ligand called BINAP. The volumetric mass density of the two enantiomers is 0.62 g.cm-3. 
 
The compound aluminium lithium bis(binaphthoxide) (ALB) is prepared by reaction of BINOL with lithium aluminium hydride.  In a different stoichiometric ratio (1:1 BINOL/LiAlH4 instead of 2:1), the chiral reducing agent BINAL (lithium dihydrido(binaphthoxy)aluminate) is produced. 
It has been employed in an asymmetric Michael reaction with cyclohexenone and dimethyl malonate  

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