ONE-POT SYNTHESIS OF 3-(PYRIDIN-2-YL)-2,3-DIHYDROAZETES <i>VIA</i> Rh(II)-CATALYZED REACTION OF DIAZOESTERS WITH TRIMETHYLSILYL-PROTECTED 2-(PYRIDIN-2-YL)-2<i>H</i>-AZIRINES
Authors
Александр Н. Коронатов
Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
Николай В. Ростовский
Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
Александр Ф. Хлебников
Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
Михаил С. Новиков
Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
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.
Author Biographies
Александр Н. Коронатов, Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
Institute of Chemistry, professor
Николай В. Ростовский, Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
Institute of Chemistry, professor
Михаил С. Новиков, Institute of Chemistry, Saint Petersburg State University,
7/9 University Embankment, Saint Petersburg 199034, Russia
