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| 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 | |
| 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. |
X Demographics
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 1 | 100% |
Demographic breakdown
| Type | Count | As % |
|---|---|---|
| Members of the public | 1 | 100% |
Mendeley readers
The data shown below were compiled from readership statistics for 82 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| United States | 2 | 2% |
| France | 1 | 1% |
| Unknown | 79 | 96% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 17 | 21% |
| Researcher | 12 | 15% |
| Student > Bachelor | 10 | 12% |
| Other | 7 | 9% |
| Student > Master | 7 | 9% |
| Other | 19 | 23% |
| Unknown | 10 | 12% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 60 | 73% |
| Pharmacology, Toxicology and Pharmaceutical Science | 1 | 1% |
| Biochemistry, Genetics and Molecular Biology | 1 | 1% |
| Business, Management and Accounting | 1 | 1% |
| Environmental Science | 1 | 1% |
| Other | 4 | 5% |
| Unknown | 14 | 17% |
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
#3,543,213
of 22,840,638 outputs
Outputs from Journal of the American Chemical Society
#12,566
of 62,032 outputs
Outputs of similar age
#63,438
of 397,005 outputs
Outputs of similar age from Journal of the American Chemical Society
#118
of 489 outputs
Altmetric has tracked 22,840,638 research outputs across all sources so far. Compared to these this one has done well and is in the 84th percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 62,032 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.8. This one has done well, scoring higher than 79% 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 397,005 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 489 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 75% of its contemporaries.