A NEW METHOD FOR THE CONVERSION OF SECONDARY AND TERTIARY AMIDES TO BRIDGED ORTHOESTERS

Authors
CHARETTE AB CHUA P
Citation
Ab. Charette et P. Chua, A NEW METHOD FOR THE CONVERSION OF SECONDARY AND TERTIARY AMIDES TO BRIDGED ORTHOESTERS, Tetrahedron letters, 38(49), 1997, pp. 8499-8502
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
49
Year of publication
1997
Pages
8499 - 8502
Database
ISI
SICI code
0040-4039(1997)38:49<8499:ANMFTC>2.0.ZU;2-I
Abstract
Secondary and tertiary amides were treated with trifluoromethanesulfon ic (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 t he corresponding 2,6,7-trioxabicyclo[2.2.2]octane orthoesters in good to excellent yields at below room temperature. (C) 1997 Elsevier Scien ce Ltd.