Squaramide-catalyzed asymmetric Michael/cyclization of 4-isothiocyanato pyrazolones and a,/3-unsaturated ketones

被引：7
作者：
Gong, Wenjing [1 ]
Du, Xin [1 ]
Wang, Wenyao [1 ]
Zhang, Wande [1 ]
Wang, Baomin [1 ]
机构：
[1] Dalian Univ Technol, Sch Chem Engn, Dept Chem, State Key Lab Fine Chem,Dept Pharmaceut Sci, Dalian 116024, Peoples R China
来源：
TETRAHEDRON LETTERS | 2021年 / 78卷
关键词：
Asymmetric catalysis; Isothiocyanato pyrazolones; Spiropyrazolones; Michael addition; ENANTIOSELECTIVE CONSTRUCTION; SPIROPYRAZOLONES; SPIROCYCLES; ANNULATION; SCAFFOLD;
D O I：
10.1016/j.tetlet.2021.153259
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cascade Michael addition/cyclization reaction of 4-isothiocyanato pyrazolones with ethyl /3-benzoylacrylates has been explored by asymmetric organocatalysis, delivering spiro[pyrazolone-pyrrolidinethione] cores bearing three contiguous stereogenic centers in excellent enantioselectivities (up to 95% ee) with excellent yields (up to 91%). This process exhibited broad substrate scope and the advantages of simple operation. A plausible mechanism for this reaction was proposed. (c) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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