Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 35, Pages 10330-10334Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701789
Keywords
alkali metals; flow chemistry; Michael addition; solid base; supported catalysts
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Japan Science and Technology Agency (JST)
- JSPS Postdoctoral Fellowship for Research in Japan
- Grants-in-Aid for Scientific Research [15F15337, 16H01006] Funding Source: KAKEN
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A novel methodology using CsF?Al2O3 as a highly efficient, environmentally benign, and reusable solid-base catalyst was developed to synthesize glutamic acid derivatives by stereoselective 1,4-addition of glycine derivatives to alpha,beta-unsaturated esters. CsF?Al2O3 showed not only great selectivity toward 1,4-addtion reactions by suppressing the undesired formation of pyrrolidine derivations by [3+2] cycloadditions, but also offered high yields for the 1,4-adduct with excellent anti diastereoselectivities. The catalyst was well characterized by using XRD, F-19 MAS-NMR and F-19 NMR spectroscopy, FT-IR, CO2-TPD, and XPS. And highly basic F from Cs3AlF6 was identified as the most probable active basic site for the 1,4-addition reactions. Continuous-flow synthesis of 3-methyl glutamic acid derivative was successfully demonstrated by using this solid-base catalysis.
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