Non-Photochemical Route to Chiral Disubstituted [7]Thiaheterohelicenes via Biaryl- and Carbonyl-Coupling Reactions
- 1 June 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (13) , 4465-4470
- https://doi.org/10.1021/jo970272t
Abstract
Non-photochemical syntheses of optically active dimethyl[7]thiaheterohelicenes (P)-(+)-14 and (M)-(−)-14 are described. The key transformations in the syntheses are the metal-mediated biaryl coupling reactions between two benzodithiophene units having oxazoline moieties and the intramolecular McMurry coupling reaction of the biaryl dialdehydes (S)-13 and (R)-13. The configuration of the atropisomer 10a obtained from the biaryl coupling reaction was shown to be S by X-ray analysis.Keywords
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