Journal
ORGANIC LETTERS
Volume 13, Issue 7, Pages 1742-1745Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol200256a
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Funding
- National Science Foundation
- NIGMS [GM72586]
- National Institutes of Health
- Colorado PEAKS AGEP
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1004924] Funding Source: National Science Foundation
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A study on the mechanism of the asymmetric intramolecular Stetter reaction is reported. This investigation includes the determination of the rate law, kinetic isotope effects, and competition experiments. The reaction was found to be first order in aldehyde and azolium catalyst or free carbene. A primary kinetic isotope effect was found for the proton of the aldehyde. Taken together with a series of competition experiments, these results suggest that proton transfer from the tetrahedral intermediate formed upon nucleophilic attack of the carbene onto the aldehyde is the first irreversible step.
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