Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates

被引：20

作者：

Curry, Lucy ^{[1
]}

Hallside, Michal S. ^{[1
]}

Powell, Luke H. ^{[1
]}

Sprague, Simon J. ^{[1
]}

Burton, Jonathan W. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

TETRAHEDRON | 2009年 / 65卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

X-RAY-DIFFRACTION; BETA-KETO-ESTERS; ACYLATION-CYCLIZATION; ORGANIC-CHEMISTRY; AMMONIUM-NITRATE; GAMMA-LACTONES; ACETATE; STEREOSELECTIVITY; MANGANESE; SOLVENT;

D O I：

10.1016/j.tet.2009.09.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective synthesis of alkenylcyclanones by the oxidative radical cyclisation of malonyl radicals onto both allenes and an allylsilane is reported, along with the diastereoselective formation of [3.3.0]-bicyclic gamma-lactones from two of these alkenylcyclanones. Furthermore, the cyclisation of 3-,4- and 5-allenyl malonates on exposure to manganese(III) acetate under both oxidative and reductive termination conditions is reported. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：10882 / 10892

页数：11

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