Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions
| Autor: | Seiji Suga, Shunsuke Irie, Koichi Mitsudo, Hiroki Mandai |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
multicomponent reaction Isocyanide Organic Chemistry Pharmaceutical Science Alcohol chiral DMAP Aldehyde Article Analytical Chemistry Kinetic resolution lcsh:QD241-441 chemistry.chemical_compound Ugi reaction lcsh:Organic chemistry chemistry Derivative (finance) Chemistry (miscellaneous) Drug Discovery Molecular Medicine Organic chemistry kinetic resolution Physical and Theoretical Chemistry |
| Zdroj: | Molecules; Volume 16; Issue 10; Pages: 8815-8832 Molecules Molecules, Vol 16, Iss 10, Pp 8815-8832 (2011) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules16108815 |
| Popis: | Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-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 α-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. |
| Databáze: | OpenAIRE |
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