Hydrolysis of Phosphonothioates with a Binaphthyl Group: P‑Stereogenic O‑Binaphthyl Phosphonothioic Acids and Their Use as Optically Active Ligands and Chiral Discriminating Agents

Hydrolysis of Phosphonothioates with a Binaphthyl Group: P‑Stereogenic O‑Binaphthyl Phosphonothioic Acids and Their Use as Optically Active Ligands and Chiral Discriminating Agents

The hydrolysis of phosphonothioates with a binaphthyl group afforded the first example of O-(2′-hydroxy)­binaphthyl phosphonothioic acids in good to high yields and >95:5 diastereoselectivity. The reaction proceeds via an axis-to-center chirality-transfer reaction. The ability of these acids to a...

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Veröffentlicht in:Organic letters 2018-03, Vol.20 (5), p.1375-1379
Hauptverfasser: Kuwabara, Kazuma, Maekawa, Yuuki, Minoura, Mao, Murai, Toshiaki
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container_title Organic letters
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creator Kuwabara, Kazuma
Maekawa, Yuuki
Minoura, Mao
Murai, Toshiaki
description The hydrolysis of phosphonothioates with a binaphthyl group afforded the first example of O-(2′-hydroxy)­binaphthyl phosphonothioic acids in good to high yields and >95:5 diastereoselectivity. The reaction proceeds via an axis-to-center chirality-transfer reaction. The ability of these acids to act as chiral molecular auxiliaries was demonstrated by using them as optically active ligands for the asymmetric ethylation of benzaldehyde and as a chiral discriminating agent for chiral aliphatic amines.
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title Hydrolysis of Phosphonothioates with a Binaphthyl Group: P‑Stereogenic O‑Binaphthyl Phosphonothioic Acids and Their Use as Optically Active Ligands and Chiral Discriminating Agents
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