173306-36-0Relevant academic research and scientific papers
Protecting group free synthesis of 6-substituted naphthols and binols
Verga, Daniela,Percivalle, Claudia,Doria, Filippo,Porta, Alessio,Freccero, Mauro
experimental part, p. 2319 - 2323 (2011/05/14)
A straightforward route for the preparation of 6-substituted naphthols and 6,6′-disubstituted binols (binol = 2,2′-dihydroxy-1,1′- binaphthyl) is presented. The synthesis has been accomplished by a one-step procedure starting from 6-bromo derivatives via direct lithiation with n-BuLi, followed by the addition of several electrophiles. This C-C functionalization has been successfully achieved with iodomethane, 3-methoxybenzaldehyde, benzophenone, methyl-2-methylbenzoate, methylbenzoate, dimethyl carbonate, ethyl 2-chloro-2-oxoacetate, and 2,2-dimethyloxirane (E). This reactivity offers a useful protecting group free synthetic protocol, toward chiral disubstituted 6,6′-binols with configuration retention of the binol moiety.
