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Updated: Aug 15, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of a Chiral Helical Molecular Template Based on
Julie Cheung1, Leslie D. Field, Trevor W. Hambley
1Department of Organic Chemistry and Department of Inorganic Chemistry, The University of Sydney, New South Wales 2006, Australia.
Abstract:
Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R(1) = R(4) = H, R(2) = R(3) = CH(3)) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diols 2, X = H. These diols proved to be configurationally stable chiral molecular templates capable of straightforward modification by attachment of molecular elements of different length and kind. The structures of the diacetate 2, X = COCH(3), and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X = p-BrC(6)H(4)CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.
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