Chiral Borinic Acid-Catalyzed Enantioselective Passerini-type Multicomponent Reaction
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.
Authors
- Mitsuhiro Arisawa (ORCID: https://orcid.org/0000-0002-7937-670X)
- Tsunayoshi Takehara (ORCID: https://orcid.org/0000-0002-4113-7578)
- Makoto Sako (ORCID: https://orcid.org/0000-0002-4268-7002)
- Shinsuke Komagawa (ORCID: https://orcid.org/0000-0002-3699-7733)
- Kenichi Murai (ORCID: https://orcid.org/0000-0002-1689-6492)
- K. Higashi
- Yuta Chikashige
- Takeyuki Suzuki
Institutions
- The University of Osaka (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-02-23
- DOI
- https://doi.org/10.1021/acs.joc.5c03042
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.00