Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 23, Pages 9721-9726Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja301685r
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Funding
- Pfizer
- Bristol-Myers Squibb
- Illinois Distinguished Fellowship
- Harold R. Snyder Fellowship
- National Science Foundation under the Center for Chemical Innovation in Stereoselective C-H Functionalization [CHE-0943980]
- Ullyot Graduate Fellowship
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0943980] Funding Source: National Science Foundation
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The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.
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