One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines

被引：4
|
作者：
Koronatov, Alexander N. [1 ]
Rostovskii, Nikolai V. [1 ]
Khlebnikov, Alexander F. [1 ]
Novikov, Mikhail S. [1 ]
机构：
[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Nab, St Petersburg 199034, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2019年 / 55卷 / 12期
基金：
俄罗斯科学基金会;
关键词：
2H-azirines; carbenoids; diazo compounds; dihydroazetes; catalysis; electrocyclization; 2H-AZIRINES; DERIVATIVES;
D O I：
10.1007/s10593-019-02599-y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot method for the synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes was developed on the basis of Rh2(esp)2-catalyzed reaction of diazoesters with 3-aryl-2-(pyridin-2-yl)-2H-azirines. To prevent deactivation of the catalyst with the pyridine-containing azirine reactant, the trimethylsilyl protection of pyridine nitrogen was used. The insertion and removal of the protecting group were carried out as a onepot synthesis. Reactions involving ethyl 2-diazo-3,3,3-trifluoropropanoate proceed stereoselectively with the formation of only the (2RS,3SR)-isomer of the dihydroazete, which is due to the thermodynamic control of the process.
引用
收藏
页码：1185 / 1189
页数：5
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