
%0 Journal Article
%A Baker, Robert W. 
%A Brkic, Zinka 
%A Sargent, Melvyn V. 
%A Skelton, Brian W. 
%A White, Allan H. 
%T Atropisomerism of 2,2'-Binaphthalenes
%J Australian Journal of Chemistry
%D 2001/05/11
%V 53
%N 12
%P 925-938
%K Asymmetric synthesis; atropomers; 2,2&#8242;-binaphthalenes; circular dichroic spectra; rotational barriers.
%R https://doi.org/10.1071/CH00122
%U https://www.publish.csiro.au/paper/CH00122 
%X The synthesis of diastereo-enriched substituted (4S)-4-isopropyl-2-(2,2&#8242;-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-&#91;2-hydroxy-1-(isopropyl)ethyl&#93;-3-methoxy-1&#8242;,N-dimethyl-2,2&#8242;-binaphthalene-1-carboxamide (22) and (R,4S)-4-isopropyl-3-methyl-2-(1&#8242;,2&#8242;,4&#8242;-trimethyl-2,2&#8242;-binaphthalen-1-yl)-4,5-dihydrooxazolium iodide (38) allowed the assignment of the absolute configurations of all the synthetic 2,2&#8242;-binaphthalenes by comparison of their c.d. spectra with those of compounds (22) and (38). 
