期刊
ACS CATALYSIS
卷 7, 期 4, 页码 2981-2989出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00562
关键词
asymmetric catalysis; supported organocatalysts; squaramides; Michael reaction; water; bioactive compounds
资金
- Russian Science Foundation [14-50-00126]
Chiral tertiary amine-derived ionic liquid supported squaramide was synthesized from available precursors and applied as an efficient organocatalyst for asymmetric Michael additions of beta-dicarbonyl compounds to alpha-nitroolefins in the presence of water. Corresponding Michael adducts were generated under proposed conditions in nearly quantitative yield with high enantioselectivity (up to 99% ee). Useful precursors to pharmaceutically important chiral beta-amino acids and anticonvulsant Pregabalin were conveniently prepared using the developed on water protocol. The catalyst is readily recoverable and reusable over 30 times without a significant decrease of catalytic reaction activity and selectivity.
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