Silicon-mediated enantioselective synthesis of structurally diverse α-amino acid derivatives
| Autor: | Guan-Wu Yin, Li Li, Xing-Feng Bai, Jian Cao, Zheng Xu, Yu-Li Sun, Ke-Fang Yang, Li-Wen Xu, Yu-Ming Cui, Jun-Han Ma |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Amino esters 010405 organic chemistry Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Cycloaddition Pyrrolidine 0104 chemical sciences Amino acid Catalysis chemistry.chemical_compound chemistry Acylsilane Bond cleavage |
| Zdroj: | Science China Chemistry. 63:1082-1090 |
| ISSN: | 1869-1870 1674-7291 |
| DOI: | 10.1007/s11426-020-9768-x |
| Popis: | The catalytic asymmetric synthesis of novel and chiral amino acid derivatives with unconventional chemo-, diastereo-, and enantio-selectivity remains a paramount challenge. Herein we reported a novel protocol for the use of highly enantioselective copper-catalyzed cycloaddition of α,β-unsaturated acylsilanes as a springboard reaction for the facile synthesis of structurally diversified pyrrolidines and complicated α-amino esters by desilylation. The newly developed process could provide a wide range of synthetically useful acylsilane-substituted pyrrolidines (ASiP) in high yields and excellent diastereo- and enantio-selectivities with Cu/(R)-XylBINAP complex as the catalyst. And the downstream desilylation transformation enables to expand the potntial applications of 1,3-dipolar cycloaddition in the construction of structurally unique amino acid derivatives, in which an unprecedented and concerted fluoride anion-promoted C–X (X=H, Si, N, C) bond cleavage occurred to the enantioselective construction of aldehyde-substituted pyrrolidines, linear cinnamaldehyde or alkene-substituted amino esters in high ee values. |
| Databáze: | OpenAIRE |
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