Bulletin of the Chemical Society of Japan p. 891 - 897 (1997)
Update date:2022-08-11
Topics:
Osuga, Hideji
Suzuki, Hitomi
Tanaka, Kazuhiko
Optically active 2-(hydroxymethyl)- and 2-(ethylthiocarbonyl)[1]benzothieno[5′,4′ :2.3][1]benzothieno [4′.5 :4,5]-thieno[3,2-f]quinolines containing π-excessive thiophene and π-deficient pyridine units were prepared by the use of exo-3-amino-2-hydroxybornane as a chiral auxiliary. This procedure consists of separation of the helical diastereomers prepared by photocyclization of 1,2-diarylethylenes and removal of the chiral auxiliary by a thiolate ion. Large scale preparation of the helicenes can be accomplished by a modified procedure of the photocyclization reaction. Optical purities of both enantiomers of 2-(hydroxymethyl)- and 2-(ethylthiocarbonyl)[1] benzothieno[5′ ,4′ : 2,3][I]benzothieno[4′.5′ : 4,5]-thieno[3,2-f lquinolines were >99.5%. Their absolute configurations were determined by comparison of CD spectra.
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