Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates

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Authors

ŠVESTKA David BOBÁĽ Pavel OTEVŘEL Jan WASER Mario

Year of publication 2024
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Pharmacy

Citation
Web https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr
Doi http://dx.doi.org/10.1021/acs.orglett.4c00818
Keywords ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL
Description The piperidine-based Takemoto catalyst has been successfully employed in a novel asymmetric transfer hydroxymethylation of activated isoindolinones, allowing us to prepare the enantioenriched hydroxymethylated adducts in good to excellent yields (48–96%) and enantiopurities (81:19–97:3 e.r.). To increase the reaction rate without compromising the selectivity, carefully optimized formaldehyde surrogates were employed, providing a convenient source of anhydrous formaldehyde with a base-triggered release. The substrate scope, including 34 entries, showed the considerable generality of the asymmetric transformation, and most entries exhibited complete conversions in 24–48 h. A scale-up experiment and multiple enantioselective downstream transformations were also carried out, suggesting the prospective synthetic utility of the products.
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