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RESEARCH PRODUCT
Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons
Alisa KoivuporrasArto ValkonenSuvi HolmstedtLijo GeorgeNuno R. Candeiassubject
Hydrosilylation010402 general chemistry01 natural sciencesBiochemistrySilyl etherchemistry.chemical_compoundredox reactionsPhysical and Theoretical Chemistryhapetus-pelkistysreaktioorgaaniset yhdisteeteetteritkemiallinen synteesi010405 organic chemistryreaction productsOrganic ChemistryhydrosilylationQuinic acidCombinatorial chemistry0104 chemical sciencesbond cleavageetherschemistryStereoselectivitySelectivityDivergent synthesisDerivative (chemistry)Vicinaldescription
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. peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-10-02 |