Asymmetric [4 + 2] annulation of 5: H -thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst
Chemical Science, ISSN: 2041-6539, Vol: 7, Issue: 9, Page: 6060-6067
2016
- 44Citations
- 19Captures
Metric Options: Counts1 Year3 YearSelecting the 1-year or 3-year option will change the metrics count to percentiles, illustrating how an article or review compares to other articles or reviews within the selected time period in the same journal. Selecting the 1-year option compares the metrics against other articles/reviews that were also published in the same calendar year. Selecting the 3-year option compares the metrics against other articles/reviews that were also published in the same calendar year plus the two years prior.
Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
Citation Benchmarking is provided by Scopus and SciVal and is different from the metrics context provided by PlumX Metrics.
Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
Citation Benchmarking is provided by Scopus and SciVal and is different from the metrics context provided by PlumX Metrics.
Metrics Details
- Citations44
- Citation Indexes44
- CrossRef44
- 44
- Captures19
- Readers19
- 19
Article Description
Versatile synthetic strategies that access diverse chemical substrates in a highly chemo- and stereo-selective manner are crucial but demanding. Construction of chiral molecules with multiple (hetero)-quaternary carbon stereocenters in a single fashion is a particularly significant challenge, with important applications in the synthesis of a range of bioactive compounds containing the 1,4-sulfur bridged piperidinone structural motif. The asymmetric synthesis of these entities is complicated due to the need to build at least two hetero-quaternary stereocenters concurrently. In order to achieve this, we have developed a new family of dipeptide-based multifunctional Brønsted base organocatalysts that are highly capable of the first asymmetric [4 + 2] annulation reaction of 5H-thiazol-4-ones with electron-deficient alkenes. This protocol could be applied to a series of alkenes such as nitroalkenes, 4-oxo-4-arylbutenones, 4-oxo-4-arylbutenoates and methyleneindolinones, providing an efficient approach to valuable chiral 1,4-sulfur bridged piperidinones and their derivatives with multiple hetereo-quaternary stereogenic centers in high yields and enantioselectivities. Density functional theory studies involving 5H-thiazol-4-one and nitroolefin catalysis propose stereochemical insights into the origin of enantio- and chemo-selectivity.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84983430639&origin=inward; http://dx.doi.org/10.1039/c6sc02039a; http://www.ncbi.nlm.nih.gov/pubmed/30034746; https://xlink.rsc.org/?DOI=C6SC02039A; http://xlink.rsc.org/?DOI=C6SC02039A; http://pubs.rsc.org/en/content/articlepdf/2016/SC/C6SC02039A; https://dx.doi.org/10.1039/c6sc02039a; https://pubs.rsc.org/en/content/articlelanding/2016/sc/c6sc02039a
Royal Society of Chemistry (RSC)
Provide Feedback
Have ideas for a new metric? Would you like to see something else here?Let us know