A new method for the conversion of secondary and tertiary amides to bridged orthoesters

Autor: André B. Charette, Peter C. Chua
Rok vydání: 1997
Předmět:
Zdroj: Tetrahedron Letters. 38:8499-8502
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10310-0
Popis: Secondary and tertiary amides were treated with trifluoromethanesulfonic (triflic) anhydride in the presence of pyridine at low temperatures to generate imino and iminium triflates. Successive treatment with 2,2-bishydroxymethyl-1-propanol in the pyridine buffered solution gave the corresponding 2,6,7-trioxabicyclo[2.2.2]octane orthoesters in good to excellent yields at below room temperature.
Databáze: OpenAIRE