Synthesis and characterization of N-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F14%3A39897792" target="_blank" >RIV/00216275:25310/14:39897792 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.3987/COM-14-13029" target="_blank" >http://dx.doi.org/10.3987/COM-14-13029</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3987/COM-14-13029" target="_blank" >10.3987/COM-14-13029</a>

Result language

angličtina

Original language name

Synthesis and characterization of N-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction

Original language description

In this paper, the preparation and characterization of eight optically pure N-functionalized (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides is described. The prepared amides and thioamides were tested as organocatalysts of aldol reaction of 4-nitrobenzaldehyde and acetone. The highest ee of formation of 4-hydroxy-4-(4-nitrophenyl)butan-2-one was obtained with (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (77% ee). The observed deceleration of the aldol reaction catalyzed in this way, as compared with that catalyzed with (S)-proline, was attributed to the formation of little reactive cyclic intermediate, which was isolated and characterized.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/EE2.3.30.0021" target="_blank" >EE2.3.30.0021: Strenthening of Research and Development Teams at the University of Pardubice</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year

2014

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Heterocycles

ISSN

0385-5414

e-ISSN

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Volume of the periodical

89

Issue of the periodical within the volume

8

Country of publishing house

JP - JAPAN

Number of pages

16

Pages from-to

1844-1859

UT code for WoS article

000342253700004

EID of the result in the Scopus database

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