Facile Asymmetric Synthesis of α,α-Disubstituted Amino Acid Derivatives with Gold Redox Catalysis Using a Chiral Auxiliary
A facile asymmetric synthesis of α,α-disubstituted amino acid derivatives was achieved via gold redox catalysis. The in situ formed aryl gold(III) served as the key intermediate toward alkyne activation. Sequential vinyl gold(III) addition to diazonium salts, followed by the gold(III) reductive elimination, yielded the α-diazo amides. The asymmetric synthesis was achieved with a selected oxazolidinone auxiliary, providing high stereoselectivity (d.r. >20:1, 99% ee). Simple derivatization afforded α,α-disubstituted peptides with good yield and good functional group diversity.
Authors
- Xiaodong Shi (ORCID: https://orcid.org/0000-0002-3189-1315)
- Peter Y. Zavalij (ORCID: https://orcid.org/0000-0001-5762-3469)
- Kai Zhao (ORCID: https://orcid.org/0000-0003-2226-806X)
- Chuan Shan (ORCID: https://orcid.org/0000-0002-5173-1335)
- Kelton Radefeld
- Qi Tang (ORCID: https://orcid.org/0009-0004-7166-7854)
- Teng Yuan (ORCID: https://orcid.org/0009-0005-1568-6492)
- Xiaohan Ye (ORCID: https://orcid.org/0000-0002-3836-4120)
- Jaclyn Bredenkamp
Institutions
- University of South Florida (US)
- University of Maryland, College Park (US)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2025-08-12
- DOI
- https://doi.org/10.1021/acscatal.5c02965
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- University of Maryland
- University of South Florida
- National Institute of General Medical Sciences