Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons
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
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Organic LettersDate
2020Copyright
© 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.
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American Chemical Society (ACS)ISSN Search the Publication Forum
1523-7060Keywords
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The Academy of Finland is duly acknowledged for financial support to N.R.C. (Decisions No. 326487 and 326486) and to A. V. (No. 314343). Finnish Cultural Foundation is acknowledged for financial support to S.H. (00190336).License
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