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@article{2390978, author = {Švestka, David and Bobáľ, Pavel and Otevřel, Jan and Waser, Mario}, article_location = {Spojené státy}, article_number = {26}, doi = {http://dx.doi.org/10.1021/acs.orglett.4c00818}, keywords = {ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL}, language = {eng}, issn = {1523-7060}, journal = {Organic Letters}, title = {Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates}, url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr}, volume = {12}, year = {2024} }
TY - JOUR ID - 2390978 AU - Švestka, David - Bobáľ, Pavel - Otevřel, Jan - Waser, Mario PY - 2024 TI - Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates JF - Organic Letters VL - 12 IS - 26 SP - 2505-2510 EP - 2505-2510 PB - American Chemical Society SN - 15237060 KW - ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr N2 - 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. ER -
ŠVESTKA, David, Pavel BOBÁĽ, Jan OTEVŘEL a Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. \textit{Organic Letters}. Spojené státy: American Chemical Society, 2024, roč.~12, č.~26, s.~2505-2510. ISSN~1523-7060. Dostupné z: https://dx.doi.org/10.1021/acs.orglett.4c00818.
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