Tetrahedron: Asymmetry

Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

T Hattori, H Iwato, K Natori, S Miyano

Index: Hattori, Tetsutaro; Iwato, Hiroaki; Natori, Koichi; Miyano, Sotaro Tetrahedron Asymmetry, 2004 , vol. 15, # 5 p. 881 - 887

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Citation Number: 7

Abstract

A convenient method is presented for the asymmetric synthesis of axially chiral 1, 1′: 5′, 1 ″-and 1, 1′: 4′, 1 ″-ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1, 5-dimenthoxynaphthalene-2, 6- dicarboxylate and its regioisomer, dimenthyl 1, 4-dimenthoxynaphthalene-2, 3- dicarboxylate, with 2-methoxynaphthalen-1-ylmagnesium bromide gave enantiomerically ...