Development of a Scalable Lanthanide Halide/Quaternary Ammonium Salt System for the Nucleophilic Addition of Grignard Reagents to Carbonyl Groups and Application to the Synthesis of a Remdesivir Intermediate

This manuscript describes the development and implementation of a scalable additive system, consisting of a lanthanide salt and a solubilizing quaternary ammonium salt, to improve the yield and robustness of the addition of an organomagnesium reagent to a ribonolactone en route to remdesivir. This s...

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Bibliographic Details
Published in:Organic process research & development 2022-03, Vol.26 (3), p.754-763
Main Authors: Stevens, Andrew C, Brak, Katrien, Bremner, W. Stacy, Brown, Angela M, Chtchemelinine, Andrei, Heumann, Lars, Kerschen, James A, Subotkowski, Witold, Vieira, Tiago, Wolfe, Lydia C, Xu, Boran, Yu, Chia-Yun
Format: Article
Language:English
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Summary:This manuscript describes the development and implementation of a scalable additive system, consisting of a lanthanide salt and a solubilizing quaternary ammonium salt, to improve the yield and robustness of the addition of an organomagnesium reagent to a ribonolactone en route to remdesivir. This system was found to be generally applicable in enhancing other challenging organomagnesium additions to enolizable and hindered carbonyl-containing compounds.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.1c00191