Tetrahedron Letters p. 4599 - 4602 (1992)
Update date:2022-08-03
Topics:
Tanaka, Kazuhiko
Osuga, Hideji
Suzuki, Hitomi
Kishida, Hiroshi
(1R,2S,3R,4S)-3-amino-2-hydroxybornane was found to be an efficient chiral auxiliary in the synthesis of functionalized heterohelicenes of high optical purity.Photocyclization of 2-(2-naphtho<2,1-b>thienylvinylene)benzo<1,2-b:4,3-b'>dithiophene-5-carboxamide afforded helicenes as a diastereomeric mixture which was readily separated by column chromatography.Removal of the chiral auxiliary from the diastereomers produced 2-methoxycarbonyl<7>heterohelicene with <α>D -2770 deg and its enantiomer with <α>D +2830 deg, respectively.
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