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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

Александр Н. Коронатов, Николай В. Ростовский, Александр Ф. Хлебников, Михаил С. Новиков
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Abstract


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 protection group were carried out as a one-pot 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.

Keywords


2H-azirines, carbenoids; dihydroazetes; diazo compounds; catalysis; electrocyclization.

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