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@proceedings{1816557,
author = {Švestka, David and Otevřel, Jan and Bobáľ, Pavel},
booktitle = {XXth INTERDISCIPLINARY MEETING OF YOUNG RESEARCHERS AND STUDENTS IN THE FIELD OF CHEMISTRY, BIOCHEMISTRY, MOLECULAR BIOLOGY, AND BIOMATERIALS},
keywords = {Amino alcohols; SMEAH; RedAl; reduction; hydroxylation; amides; nitriles},
language = {eng},
title = {One-pot synthesis of 1-aryl-2-amino alcohols from the corresponding amides or nitriles},
url = {http://www.interdisciplinarymeeting.cz/2021/shell/sbornik-2021.pdf},
year = {2021}
}
TY - CONF
ID - 1816557
AU - Švestka, David - Otevřel, Jan - Bobáľ, Pavel
PY - 2021
TI - One-pot synthesis of 1-aryl-2-amino alcohols from the corresponding amides or nitriles
KW - Amino alcohols
KW - SMEAH
KW - RedAl
KW - reduction
KW - hydroxylation
KW - amides
KW - nitriles
UR - http://www.interdisciplinarymeeting.cz/2021/shell/sbornik-2021.pdf
N2 - We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C–H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target.
ER -
ŠVESTKA, David, Jan OTEVŘEL and Pavel BOBÁĽ. One-pot synthesis of 1-aryl-2-amino alcohols from the corresponding amides or nitriles. In \textit{XXth INTERDISCIPLINARY MEETING OF YOUNG RESEARCHERS AND STUDENTS IN THE FIELD OF CHEMISTRY, BIOCHEMISTRY, MOLECULAR BIOLOGY, AND BIOMATERIALS}. 2021.
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