Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization

Stefan Berlin; Cecilia Ericsson; Lars Engman

doi:10.1021/ol016127q

Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization

Org Lett. 2002 Jan 10;4(1):3-6. doi: 10.1021/ol016127q.

Authors

Stefan Berlin¹, Cecilia Ericsson, Lars Engman

Affiliation

¹ Uppsala University, Institute of Chemistry, Department of Organic Chemistry, Box 531, S-751 21, Uppsala, Sweden.

PMID: 11772076
DOI: 10.1021/ol016127q

Abstract

[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.