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

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...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 2; pp. 498 - 501
Main Authors Eddy, Nicholas A, Kelly, Christopher B, Mercadante, Michael A, Leadbeater, Nicholas E, Fenteany, Gabriel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.01.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclopentanes - chemistry
Ketones - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Quaternary Ammonium Compounds - chemistry
Science & Technology
KETONES
DIELS-ALDER REACTIONS
ESTERS
ALLYLIC SUBSTITUENTS
CHIRAL DIENES
SELECTIVITY
GREEN
PRIMARY ALCOHOLS
OXIDANTS
WATER
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Summary: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 Diels–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.
Bibliography:NIH RePORTER
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2030873