Atropisomerism of 2,2'-binaphthalenes

R.W. Baker, Z. Brkic, Z. Brkic, M.V. Sargent, M.V. Sargent, Brian Skelton, Allan White

Research output: Contribution to journalArticle

14 Citations (Scopus)


The synthesis of diastereo-enriched substituted (4S)-4-isopropyl-2-(2,2'-binaphthalen-1-yl)-4,5-dihydrooxazoles from substituted 2-naphthalenylmagnesium bromides and (4S)-4-isopropyl-2-(2-methoxynaphthalen-1-yl)-4,5-dihydrooxazole (4) and (4S)-4-isopropyl-2-(2,3-dimethoxynaphthalen-1-yl)-4,5-dihydrooxazole (5) is described. The product oxazolines were converted into a number of derivatives and the free energy barriers to internal rotation of several of these derivatives were determined. The determination of the X-ray crystal structures and the c.d. spectra of (S,1S)-N-[2-hydroxy-1-(isopropyl)ethyl]-3-methoxy-1',N-dimethyl-2,2'-binaphthalene-1-carboxamide (22) and (R,4S)-4-isopropyl-3-methyl-2-(1',2',4'-trimethyl-2,2'-binaphthalen-1-yl)-4, 5-dihydrooxazolium iodide (38) allowed the assignment of the absolute configurations of all the synthetic 2,2'-binaphthalenes by comparison of their c.d. spectra with those of compounds (22) and (38).
Original languageEnglish
Pages (from-to)925-938
JournalAustralian Journal of Chemistry
Issue numberN/A
Publication statusPublished - 2000

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