通过自由基羰基化/还原环化反应，由容易获得的有机硫属元素前体构建四氢呋喃-3-酮。

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

作者信息

Berlin Stefan, Ericsson Cecilia, Engman Lars

机构信息

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

出版信息

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

DOI:10.1021/ol016127q

PMID:11772076

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.

摘要

[反应：见正文] β-羟烷基芳基硫属化合物可通过环氧化物与亲核苯硒醇盐或碲醇盐的区域选择性开环反应轻松制得，用丙炔酸乙酯或（E）-1,2-双（苯磺酰基）乙烯处理可使其发生O-烷基化反应。随后，在偶氮二异丁腈/三（三甲硅基）硅烷和一氧化碳（80个大气压）存在下进行羰基化/还原环化反应，以中等至良好的产率得到四氢呋喃-3-酮。