Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons
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
CCDC 2005907: Experimental Crystal Structure Determination
Related Article: Suvi Holmstedt, Lijo George, Alisa Koivuporras, Arto Valkonen, Nuno R. Candeias|2020|Org.Lett.|22|8370|doi:10.1021/acs.orglett.0c02995