Chiral Auxiliary-Directed Site-Selective Deprotonation of the Cubane Skeleton

The first diastereoselective synthesis of trisubstituted cubanes was achieved using a chiral auxiliary. To establish chirality within the cubane skeleton, at least three substituents must be introduced at the appropriate positions. Ready conversion of cubane carboxylic acid to a chiral amide followe...

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Bibliographic Details
Published in:Organic letters 2023-01, Vol.25 (1), p.27-30
Main Authors: Takebe, Hiyori, Yoshino, Nana, Shimada, Yukako, Williams, Craig M., Matsubara, Seijiro
Format: Article
Language:English
Subjects:
Amides
Carboxylic Acids
Molecular Structure
Skeleton
Stereoisomerism
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Summary:The first diastereoselective synthesis of trisubstituted cubanes was achieved using a chiral auxiliary. To establish chirality within the cubane skeleton, at least three substituents must be introduced at the appropriate positions. Ready conversion of cubane carboxylic acid to a chiral amide followed by sequential ortho-selective deprotonations and electrophilic trapping afforded the corresponding 1,2,3-trisubstituted cubanes with high diastereoselectivity. This route opens new possibilities for the preparation of enantio-enriched cubanes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03659