Double 1,3-Dipolar Cycloadditions of Two Nonstabilized Azomethine Ylides for Polycyclic Pyrrolidines

被引:21
作者
Zhang, Xiaofeng [1 ,2 ]
Qiu, Weiqi [1 ,2 ]
Evans, Jason [1 ,2 ]
Kaur, Manpreet [3 ]
Jasinski, Jerry P. [3 ]
Zhang, Wei [1 ,2 ]
机构
[1] Univ Massachusetts, Ctr Green Chem, 100 Morrissey Blvd, Boston, MA 02125 USA
[2] Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA
[3] Keene State Coll, Dept Chem, 229 Main St, Keene, NH 03435 USA
关键词
X=Y-ZH SYSTEMS; ONE-POT; INTRAMOLECULAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; DECARBOXYLATIVE ROUTE; POTENTIAL 1,3-DIPOLES; 2-AZAALLYL ANIONS; GENERATION; CONSTRUCTION; AZIRIDINES;
D O I
10.1021/acs.orglett.9b00487
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nonstabilized azomethine ylides derived from decarboxylation of oxazolidin-5-ones were used for double 1,3-dipolar cycloadditions in diastereoselective synthesis of pyrrolidine-containing tetracyclic compounds. This is the first example of one-pot and five-component reactions involving two nonstabilized azomethine ylides. Only CO2 and water were generated as byproducts.
引用
收藏
页码:2176 / 2179
页数:4
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