Asymmetric α-Allylation of Amino Acid Esters with Alkynes Enabled by Chiral Aldehyde/Palladium Combined Catalysis
A highly efficient, atom-economical α-allylation reaction of NH<sub>2</sub>-unprotected amino acid esters and alkynes is achieved by chiral aldehyde/palladium combined catalysis. A diverse range of α,α-disubstituted nonproteinogenic α-amino acid esters are produced in 31-92% yields and 84-97% ee values. The allylation products are utilized for the synthesis of drug molecule BMS561392 and other chiral molecules possessing complex structures. Mechanistic investigations reveal that this reaction proceeds via a chiral aldehyde-/palladium-mediated triple cascade catalytic cycle.
Authors
- Fang Zhu (ORCID: https://orcid.org/0000-0002-6939-9975)
- Chao-Xing Li
- Zhu‐Lian Wu (ORCID: https://orcid.org/0000-0001-8444-4028)
- Jianhua Liu (ORCID: https://orcid.org/0000-0002-5894-3912)
- Wen Wei (ORCID: https://orcid.org/0000-0001-5100-8545)
- Chenjiang Liu (ORCID: https://orcid.org/0000-0002-8241-0809)
- Yao Lin
- Tian Cai (ORCID: https://orcid.org/0000-0002-9668-6750)
- Qi‐Xiang Guo (ORCID: https://orcid.org/0000-0002-0405-7958)
Institutions
- Southwest University (CN)
- Xinjiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c02840
- Citations
- 6
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- National Natural Science Foundation of China
- Southwest University
- Fundamental Research Funds for the Central Universities