A straightforward synthesis in aqueous medium of enantiomerically. Enriched S(-)2,2'-dihydroxy-1,1'-binaphthyl.
Chiral, atropisomeric 2,2'-dihydroxy-1,1'-binaphthyl has been extensively used to direct asymmetric processes. Its key role in asymmetric catalysis has spurred efforts to synthesize it in the optically pure form, but the reported synthetic routes have a significant environmental impact. In an aqueous peroxydase-cyclodextrin system the oxidative coupling of 2-naphthol took place very rapidly in almost quantitative yield and resulted in an enantiomeric excess. This one-pot synthesis do not require any organic solvents and oxidising metal cations.
Trotta
Francesco
F
Dipartimento di Chimica Inorganica, Chimica Fisica e Chimica dei Materiali dell'Universitiá di Torino, Via Pietro Giuria 7, 1-10125 Torino, Italy. francesco.trotta@unito.it
Cravotto
Giancarlo
G
Casile
Giovanni
G
D002384:Catalysis; D003505:Cyclodextrins / Q000737:chemistry*; D006801:Humans; D009281:Naphthalenes / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D014873:Water Pollutants; D014877:Water Pollution, Chemical / Q000517:prevention & control
D003505:Cyclodextrins; D009281:Naphthalenes; D009284:Naphthols; C475744:S(-)2,2'-dihydroxy-1,1'-binaphthyl; D012997:Solvents; D014873:Water Pollutants; C028405:2-naphthol; C412330:1,1'-binaphthyl