Diastereo- and Enantioselective Synthesis of Quaternary α-Amino Acid Precursors by Copper-Catalyzed Propargylation
| Autor: | Congzheng Gu, Ye Xu, Wu Xiaoyu, Beibei Meng, Qiongqiong Zhu, Chuanhu Lei, Jie Chen |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Substitution reaction Molecular Structure 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Alkyne Stereoisomerism 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Stereocenter Adduct Amino acid Pargyline chemistry Moiety Amino Acids Physical and Theoretical Chemistry Copper |
| Zdroj: | Organic Letters. 21:9985-9989 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b03894 |
| Popis: | A diastereo- and enantioselective propargylic substitution reaction between propargylic carbonates and α-substituted nitroacetates catalyzed by a Cu-pybox complex is described. This method allows the preparation of a series of non-proteinogenic quaternary α-amino acid precursors featuring two contiguous stereogenic centers and a terminal alkyne moiety in high yields with good to excellent diastereo- and enantioselectivities in most cases. The propargylated adducts were elaborated into a diverse set of quaternary α-amino acid derivatives. |
| Databáze: | OpenAIRE |
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