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 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.

Citation

Hiyori Takebe, Nana Yoshino, Yukako Shimada, Craig M Williams, Seijiro Matsubara. Chiral Auxiliary-Directed Site-Selective Deprotonation of the Cubane Skeleton. Organic letters. 2023 Jan 13;25(1):27-30

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PMID: 36594869

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