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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 and Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. \textit{Organic Letters}. Spojené státy: American Chemical Society, 2024, vol.~12, No~26, p.~2505-2510. ISSN~1523-7060. Available from: https://dx.doi.org/10.1021/acs.orglett.4c00818.
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