Access to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt

被引：26

作者：

Eddy, Nicholas A. ^{[1
]}

Kelly, Christopher B. ^{[1
]}

Mercadante, Michael A. ^{[1
]}

Leadbeater, Nicholas E. ^{[1
]}

Fenteany, Gabriel ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

DIELS-ALDER REACTIONS; ALLYLIC SUBSTITUENTS; PRIMARY ALCOHOLS; CHIRAL DIENES; SELECTIVITY; GREEN; OXIDANTS; KETONES; ESTERS; WATER;

D O I：

10.1021/ol2030873

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diets-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.

引用

页码：498 / 501

页数：4

共 34 条

[21] 4-AcNH-TEMPO-catalyzed oxidation of aldoses to aldaric acids using chlorine or bromine as terminal oxidants [J].