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Chiral borinic acid catalyzes the Passerini-type reaction to create α-hydroxy amides, suggesting efficient synthesis methods.
We report a chiral borinic acid-catalyzed enantioselective Passerini-type reaction of aldehydes with isocyanides and water to furnish α-hydroxy amides. The reaction proceeds under mild conditions and provides high efficiency and moderate to good enantioselectivity, especially with aliphatic aldehydes. Mechanistic studies are consistent with a monomeric borinic acid species as the catalytically active form. A reactivity profile distinct from previous methodologies is observed.
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Higashi et al. (2026) studied this question.
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