文献类型：期刊文献

英文题名：Enantioselective Synthesis of Spirooxindoles: Asymmetric [3+2] Cycloaddition of (3-Isothiocyanato)oxindoles with Azodicarboxylates

作者：Jiang, Yu[1,2];Pei, Cheng-Kui[1,2];Du, Dan[1,2];Li, Xiao-Ge[3];He, Ya-Nan[4];Xu, Qin[1,2];Shi, Min[1,2,5]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China;[4]BioTools Inc, Jupiter, FL 33458 USA;[5]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

年份：2013

卷号：2013

期号：35

起止页码：7895

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000327775800008)，CCR-EXPANDED(收录号:WOS:000327775800008)】；

基金：We thank the Shanghai Municipal Committee of Science and Technology (11JC1402600), the National Basic Research Program of China [(973)-2010CB833302], the Fundamental Research Funds for the Central Universities, and the National Natural Science Foundation of China (21072206, 21102166, 20472096, 20872162, 20672127, 21121062, and 20732008) for financial support. We also thank Mr. Luo for evaluating the biological activities of the products.

语种：英文

外文关键词：Cycloaddition; Alkaloids; Organocatalysis; (3-Isothiocyanato)oxindoles; Azodicarboxylates; Spirooxindoles

摘要：The catalytic asymmetric [3+2] cycloaddition of (3-isothiocyanato)oxindoles with azodicarboxylates has been explored in the presence of (DHQD)(2)PHAL. It affords spirooxindoles having two heterocycles at their C3-position in excellent yields, with high enantioselectivities, and under mild conditions within 5 min. Moreover, another spirooxindole derived from the reaction of (3-isothiocyanato)oxindole with two molecules of azodicarboxylate could also be formed in excellent yields with the same high enantioselectivities under the standard conditions.