期刊
MOLECULES
卷 16, 期 10, 页码 8815-8832出版社
MDPI
DOI: 10.3390/molecules16108815
关键词
multicomponent reaction; Ugi reaction; chiral DMAP; kinetic resolution
资金
- Japan Society for the Promotion of Science (JSPS) [21850020]
- Okayama Foundation for Science and Technology
- Wesco Scientific Promotion
- Okayama University
- Grants-in-Aid for Scientific Research [23750113, 21850020, 22106533] Funding Source: KAKEN
Diastereoselective Ugi reactions of DMAP-based aldehydes with alpha-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various alpha-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of alpha-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.
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