[PMID]: | 29379007 |
[Au] Autor: | Ye CX; Melcamu YY; Li HH; Cheng JT; Zhang TT; Ruan YP; Zheng X; Lu X; Huang PQ |
[Ad] Endereço: | Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, China. |
[Ti] Título: | Dual catalysis for enantioselective convergent synthesis of enantiopure vicinal amino alcohols. |
[So] Source: | Nat Commun;9(1):410, 2018 01 29. |
[Is] ISSN: | 2041-1723 |
[Cp] País de publicação: | England |
[La] Idioma: | eng |
[Ab] Resumo: | Enantiopure vicinal amino alcohols and derivatives are essential structural motifs in natural products and pharmaceutically active molecules, and serve as main chiral sources in asymmetric synthesis. Currently known asymmetric catalytic protocols for this class of compounds are still rare and often suffer from limited scope of substrates, relatively low regio- or stereoselectivities, thus prompting the development of more effective methodologies. Herein we report a dual catalytic strategy for the convergent enantioselective synthesis of vicinal amino alcohols. The method features a radical-type Zimmerman-Traxler transition state formed from a rare earth metal with a nitrone and an aromatic ketyl radical in the presence of chiral N,N'-dioxide ligands. In addition to high level of enantio- and diastereoselectivities, our synthetic protocol affords advantages of simple operation, mild conditions, high-yielding, and a broad scope of substrates. Furthermore, this protocol has been successfully applied to the concise synthesis of pharmaceutically valuable compounds (e.g., ephedrine and selegiline). |
[Mh] Termos MeSH primário: |
Aldeídos/química Amino Álcoois/síntese química Técnicas de Química Sintética Ácidos de Lewis/química Óxidos de Nitrogênio/química
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[Mh] Termos MeSH secundário: |
Catálise Luz Oxirredução Processos Fotoquímicos Estereoisomerismo
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[Pt] Tipo de publicação: | JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T |
[Nm] Nome de substância:
| 0 (Aldehydes); 0 (Amino Alcohols); 0 (Lewis Acids); 0 (Nitrogen Oxides); 0 (nitrones) |
[Em] Mês de entrada: | 1802 |
[Cu] Atualização por classe: | 180227 |
[Lr] Data última revisão:
| 180227 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 180131 |
[St] Status: | MEDLINE |
[do] DOI: | 10.1038/s41467-017-02698-4 |
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