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Isotope Effects Reveal the Mechanism of Enamine Formation in l-Proline-Catalyzed α-Amination of Aldehydes

Overview of attention for article published in Journal of the American Chemical Society, February 2016
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About this Attention Score

  • In the top 25% of all research outputs scored by Altmetric
  • High Attention Score compared to outputs of the same age (86th percentile)
  • High Attention Score compared to outputs of the same age and source (83rd percentile)

Mentioned by

blogs
1 blog
twitter
2 tweeters

Citations

dimensions_citation
10 Dimensions

Readers on

mendeley
56 Mendeley

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Summary Blogs Twitter Dimensions citations
Title
Isotope Effects Reveal the Mechanism of Enamine Formation in l-Proline-Catalyzed α-Amination of Aldehydes
Published in
Journal of the American Chemical Society, February 2016
DOI 10.1021/jacs.5b10876
Pubmed ID
26772311
Authors

Melissa A. Ashley, Jennifer S. Hirschi, Joseph A. Izzo, Mathew J. Vetticatt

Abstract

The mechanism of L-proline catalyzed α-amination of 3-phenylpropionaldehyde was studied using a combination of experimental kinetic isotope effects (KIEs) and theoretical calculations. Observation of a significant carbonyl 13C KIE and a large primary (1°) α-deuterium KIE support rate-determining enamine formation. Theoretical predictions of KIEs exclude the widely accepted mechanism - enamine formation via intramolecular deprotonation of an iminium carboxylate intermediate (7). An E2-elimination mechanism catalyzed by a bifunctional base, that directly forms an N-protonated enamine species (12•H+) from an oxazolidinone (11) intermediate, accounts for the experimental KIEs. These findings provide the first experimental picture of the transition state geometry of enamine formation and clarify the role of oxazolidinones as non-parasitic intermediates in proline catalysis.

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Twitter Demographics

The data shown below were collected from the profiles of 2 tweeters who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 56 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
United States 2 4%
France 1 2%
Unknown 53 95%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 15 27%
Researcher 11 20%
Student > Bachelor 8 14%
Other 4 7%
Student > Master 4 7%
Other 10 18%
Unknown 4 7%
Readers by discipline Count As %
Chemistry 45 80%
Agricultural and Biological Sciences 1 2%
Biochemistry, Genetics and Molecular Biology 1 2%
Physics and Astronomy 1 2%
Social Sciences 1 2%
Other 1 2%
Unknown 6 11%

Attention Score in Context

This research output has an Altmetric Attention Score of 10. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 05 February 2016.
All research outputs
#1,343,691
of 12,368,126 outputs
Outputs from Journal of the American Chemical Society
#3,948
of 45,992 outputs
Outputs of similar age
#45,525
of 331,508 outputs
Outputs of similar age from Journal of the American Chemical Society
#70
of 436 outputs
Altmetric has tracked 12,368,126 research outputs across all sources so far. Compared to these this one has done well and is in the 89th percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 45,992 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 5.3. This one has done particularly well, scoring higher than 91% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 331,508 tracked outputs that were published within six weeks on either side of this one in any source. This one has done well, scoring higher than 86% of its contemporaries.
We're also able to compare this research output to 436 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 83% of its contemporaries.

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