Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn-Selective Henry Reaction

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F17%3A43876074" target="_blank" >RIV/62157124:16370/17:43876074 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1055/s-0036-1588594" target="_blank" >http://dx.doi.org/10.1055/s-0036-1588594</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1055/s-0036-1588594" target="_blank" >10.1055/s-0036-1588594</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn-Selective Henry Reaction

Popis výsledku v původním jazyce

A scalable, efficient and chromatography-free synthesis of a new enantiopure C-2-symmetric bis(thiourea) catalyst was accomplished from a readily available starting material. The developed strategy could be conducted on a multi-gram scale. Both the prepared enantiomers of the bis(thiourea) organocatalyst have been tested in the asymmetric Henry reaction under thoroughly optimized conditions during which an unusual solvent effect on enantioselectivity was found. The corresponding adducts were obtained in excellent yields with good to excellent enantioselectivities. The achieved high reactivity and enantioselectivity in the nitroaldol reaction of nitroalkanes with aromatic aldehydes suggests promising potential for this catalyst. Moreover, a significant syn-diastereoselectivity was observed.

Název v anglickém jazyce

Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn-Selective Henry Reaction

Popis výsledku anglicky

A scalable, efficient and chromatography-free synthesis of a new enantiopure C-2-symmetric bis(thiourea) catalyst was accomplished from a readily available starting material. The developed strategy could be conducted on a multi-gram scale. Both the prepared enantiomers of the bis(thiourea) organocatalyst have been tested in the asymmetric Henry reaction under thoroughly optimized conditions during which an unusual solvent effect on enantioselectivity was found. The corresponding adducts were obtained in excellent yields with good to excellent enantioselectivities. The achieved high reactivity and enantioselectivity in the nitroaldol reaction of nitroalkanes with aromatic aldehydes suggests promising potential for this catalyst. Moreover, a significant syn-diastereoselectivity was observed.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

SYNTHESIS

ISSN

0039-7881

e-ISSN

—

Svazek periodika

49

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

593-603

Kód UT WoS článku

000393233000019

EID výsledku v databázi Scopus

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