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

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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 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.

Original languageEnglish
Pages (from-to) 1185–1189
Number of pages5
JournalChemistry of Heterocyclic Compounds
Volume55
Issue number12
DOIs
Publication statusPublished - 27 Dec 2019

Scopus subject areas

  • Chemistry(all)

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