Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization.
[reaction: see text] beta-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.
Berlin
Stefan
S
Uppsala University, Institute of Chemistry, Department of Organic Chemistry, Box 531, S-751 21, Uppsala, Sweden.
Ericsson
Cecilia
C
Engman
Lars
L