Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons
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
Published inOrganic Letters
Embargoed until: 2021-10-02Request copy from author
© 2020 American Chemical Society
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.