Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester.
Two ways for the synthesis of binaphthyl were examined based on a chiral ligand-mediated asymmetric conjugate addition of 1-naphthyllithium to naththalene-2-carboxylic acid 2,6-di-t-butyl-4-methoxyphenyl esters. The one pot method by conjugate addition-elimination gave a relatively higher enantioselectivity than the two step synthesis based on addition and subsequent oxidative aromatization.
Shindo
Mitsuru
M
Institute for Materials Chemistry and Engineering, Kyushu University.
Yamamoto
Yasutomo
Y
Yamada
Ken-Ichi
K
Tomioka
Kiyoshi
K
D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*
D009281:Naphthalenes; C542457:naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester; C542456:naphthyllithium