Facile domino access to chiral mono-, bi-, and tricyclic 2,3-dihydrofurans |
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| Authors: | Fan Li-Ping Li Ping Li Xin-Sheng Xu Dong-Cheng Ge Meng-Meng Zhu Wei-Dong Xie Jian-Wu |
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| Institution: | Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, 321004 Jinhua, PR China. |
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| Abstract: | The asymmetric domino Michael-S(N)2 reaction of various 1,3-dicarbonyl compounds to α-bromonitroalkenes is described for the first time, employing readily available cinchona-derived bifunctional thioureas as organocatalysts. The novel transformations were highly regio-, chemo-, diastereo-, and enantioselective, which simultaneously gave the chiral tricyclic 2,3-dihydrofurans, bicyclic 2,3-dihydrofurans, and tetrasubstituted 2,3-dihydrofurans with two vicinal chiral carbon centers. |
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