Formate ester synthesis via reaction of 2-bromoethylamines with dimethylformamide

Marianna Dakanali, George K. Tsikalas, Harald Krautscheid, Haralambos E. Katerinopoulos

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

2-Bromoethylamines are converted to the corresponding formate esters in the presence of DMF. Both primary and secondary bromides are smoothly transformed to the esters in satisfactory yields. The reaction mechanism involves the formation of an aziridinium ion, which upon reaction with DMF forms a Vilsmeier-type intermediate that is further hydrolyzed to the corresponding formates. Participation of the β-amino group appears to control not only the regioselectivity but also the stereoselectivity of the reaction. Application of the reaction conditions to chiral substrates indicated that non-rearranged products are formed with retention of configuration at the reacting center.

Original languageEnglish (US)
Pages (from-to)1648-1651
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number10
DOIs
StatePublished - Mar 3 2008

Keywords

  • 2-Bromoethylamines
  • Aziridinium ion
  • Formate esters
  • Vilsmeier-intermediate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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