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Isotope Effects Reveal 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, January 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 (84th percentile)
  • High Attention Score compared to outputs of the same age and source (80th percentile)

Mentioned by

blogs
1 blog
twitter
1 tweeter

Readers on

mendeley
37 Mendeley

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Title
Isotope Effects Reveal Mechanism of Enamine Formation in L-Proline Catalyzed α-Amination of Aldehydes.
Published in
Journal of the American Chemical Society, January 2016
DOI 10.1021/jacs.5b10876
Pubmed ID
26772311
Authors

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

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 profile of 1 tweeter 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 37 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Germany 2 5%
United States 2 5%
France 1 3%
Unknown 32 86%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 11 30%
Student > Bachelor 6 16%
Researcher 6 16%
Student > Master 4 11%
Professor > Associate Professor 3 8%
Other 7 19%
Readers by discipline Count As %
Chemistry 34 92%
Environmental Science 1 3%
Agricultural and Biological Sciences 1 3%
Physics and Astronomy 1 3%

Attention Score in Context

This research output has an Altmetric Attention Score of 9. 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 04 February 2016.
All research outputs
#882,572
of 7,688,550 outputs
Outputs from Journal of the American Chemical Society
#2,557
of 18,319 outputs
Outputs of similar age
#48,766
of 323,251 outputs
Outputs of similar age from Journal of the American Chemical Society
#72
of 368 outputs
Altmetric has tracked 7,688,550 research outputs across all sources so far. Compared to these this one has done well and is in the 88th percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 18,319 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 5.1. This one has done well, scoring higher than 85% 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 323,251 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 84% of its contemporaries.
We're also able to compare this research output to 368 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 80% of its contemporaries.

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