A1 Journal article (refereed)
Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons (2020)


Holmstedt, Suvi; George, Lijo; Koivuporras, Alisa; Valkonen, Arto; Candeias, Nuno R. (2020). Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons. Organic Letters, 22 (21), 8370-8375. DOI: 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

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

Open Access: Publication channel is not openly available


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
Academy of Finland
01/01/2018-31/12/2020


Ministry reporting: Yes

Preliminary JUFO rating: 2


Last updated on 2020-09-11 at 09:57