Maki and Scheidt
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In summary, saturated esters are produced in a single flask from a wide variety of aldehydes
by a carbene-catalyzed oxidation. In this process, the N-heterocyclic carbene catalyst formed
in situ undergoes addition to a saturated aldehyde and the aromatic framework of the catalyst
activates the carbinol intermediate generated in situ for a mild manganese(IV) oxidation. The
scope of the reaction includes electron-rich heterocyclic aldehydes and substrates containing
potentially sensitive stereochemistry. Further investigations capitalizing on the unique aspects
of carbene catalysis for oxidations and reductions are underway and will be reported in due
course.
Supplementary Material
Refer to Web version on PubMed Central for supplementary material.
Acknowledgment
Research support was generously provided by NIH/NIGMS (GM73072), Abbott Laboratories, Amgen, AstraZeneca,
GlaxoSmithKline, the Sloan Foundation, and Boehringer-Ingelheim. B. E. M. was supported by a GAANN Fellowship.
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2
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