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

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Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 2