Format

Send to

Choose Destination
Org Lett. 2012 Jan 20;14(2):498-501. doi: 10.1021/ol2030873. Epub 2011 Dec 29.

Access to dienophilic ene-triketone synthons by oxidation of diketones with an oxoammonium salt.

Author information

1
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA.

Abstract

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.

PMID:
22206582
PMCID:
PMC3459679
DOI:
10.1021/ol2030873
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center