期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 46, 页码 24456-24460出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202110321
关键词
2-aminotetralin; 3-aminochroman; chiral amines; imine reductase; reductive amination
资金
- Nouryon
- UK Biotechnology and Biological Sciences Research Council (BBSRC)
- Industrial Biotechnology Innovation Centre (IBioIC)
- BBSRC
- European Research Council (ERC) [742987]
The efficient biocatalytic approach for the synthesis of 2-aminotetralin and 3-aminochroman derivatives was reported, achieving high yields and enantioselectivity for over 15 examples. Additionally, a chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine was successfully accomplished with a 63% overall yield and 92% ee.
2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine in 63 % overall yield and 92 % ee.
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