Highly enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by designer chiral BINOL–quinine–squaramide: efficient access to optically active nitro-alkanes and their isoxazole derivatives |
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| Authors: | Bin Liu Xin Han Ze Dong Hao Lv Hai-Bing Zhou Chune Dong |
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| Institution: | Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, State Key Laboratory of Virology, Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China |
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| Abstract: | A chiral BINOL–quinine–squaramide has been identified as the best catalyst for the asymmetric Michael addition of nitroalkenes to 1,3-dicarbonyl compounds. A series of chiral nitroalkanes were prepared with approximately >99% ee. Furthermore, the methodology was applied successfully to the synthesis of enantiomerically pure isoxazoles derivatives (>99% ee). |
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