A1 Journal article (refereed)
Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons (2020)
Holmstedt, S., George, L., Koivuporras, A., Valkonen, A., & Candeias, N. R. (2020). Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons. Organic Letters, 22(21), 8370-8375. https://doi.org/10.1021/acs.orglett.0c02995
JYU authors or editors
Publication details
All authors or editors: Holmstedt, Suvi; George, Lijo; Koivuporras, Alisa; Valkonen, Arto; Candeias, Nuno R.
Journal or series: Organic Letters
ISSN: 1523-7060
eISSN: 1523-7052
Publication year: 2020
Publication date: 01/10/2020
Volume: 22
Issue number: 21
Pages range: 8370-8375
Publisher: American Chemical Society (ACS)
Publication country: United States
Publication language: English
DOI: https://doi.org/10.1021/acs.orglett.0c02995
Publication open access: Not open
Publication channel open access:
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/73916
Abstract
The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.
Keywords: chemical synthesis; oxidation-reduction reaction; organic compounds; ethers
Free keywords: redox reactions; reaction products; bond cleavage; ethers; hydrosilylation
Contributing organizations
Related projects
- Robust S...I+...S Halogen Bonded Supramolecular Assemblies (research costs)
- Valkonen, Arto
- Research Council of Finland
Ministry reporting: Yes
Reporting Year: 2020
JUFO rating: 2