Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, 321004 Jinhua, PR China.
J Org Chem. 2010 Dec 17;75(24):8716-9. doi: 10.1021/jo101935k. Epub 2010 Nov 23.
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.
首次报道了各种 1,3-二羰基化合物与α-溴代硝基烯烃的不对称多米诺迈克尔-S(N)2 反应，使用易得的金鸡纳衍生双功能硫脲作为有机催化剂。这些新颖的转化具有高度的区域选择性、化学选择性、非对映选择性和对映选择性，同时生成了手性三环 2,3-二氢呋喃、双环 2,3-二氢呋喃和具有两个相邻手性碳原子的四取代 2,3-二氢呋喃。
