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Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge–accelerated sulfonium rearrangement
Open accessAbstract
Four varieties of carbonyl sandwich: Compounds with adjacent carbons sandwiched between two carbonyl (C=O) centers turn up frequently in organic chemistry. When these central carbons each have a substituent, there are four possible mutual geometries, all with potentially distinct biochemical properties. Kaldre et al. present a single method to access each stereoisomer individually. The outcome depends on the straightforwardly tunable configuration of a sulfoxide group in a precursor, which guides a rearrangement. The versatility of the method should facilitate selective access to 1,4-dicarbonyl motifs in pharmaceutical research. Science , this issue p. 664
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OLEX2 : a complete structure solution, refinement and analysis program
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., & Puschmann, H. (2009) · Journal of Applied Crystallography · doi:10.1107/s0021889808042726 · Cited by 32,811
Cited by
Kaiser, D., Klose, I., Oost, R., Neuhaus, J., & Maulide, N. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00111 · Cited by 887
Self-citationReversal of Regioselectivity in Ynamide Chemistry
Zhou, B., Tan, T.-D., Zhu, X.-Q., Shang, M., & Ye, L.-W. (2019) · ACS Catalysis · doi:10.1021/acscatal.9b01851 · Cited by 294
Metadata
- Authors
- Kaldre, D., Klose, I., & Maulide, N.
- Venue
- Science
- Published
- 2018-08-17
- Volume
- 361
- Issue
- 6403
- Pages
- 664-667
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2887055365
- Cited by
- 233
- References
- 1
- FWCI
- 11.34
- Type
- journal article
- Language
- en
- Open access
- green
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- Kaldre, D., Klose, I., & Maulide, N. (2018). Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge–accelerated sulfonium rearrangement. Science. https://doi.org/10.1126/science.aat5883
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