Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions

Kód výsledku v IS VaVaI

RIV/00216275:25310/17:39902351 - isvavai.cz

Výsledek na webu

https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588107

DOI - Digital Object Identifier

10.1055/s-0036-1588107

Jazyk výsledku

angličtina

Název v původním jazyce

Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions

Popis výsledku v původním jazyce

A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared amines were screened as organocatalysts in the direct asymmetric aldol reaction between 4-nitrobenzaldehyde or isatin and acetone or cyclohexanone. The aldol adducts were obtained in good chemical yields, diastereoselectivity¬ up to 97:3 (reactions with cyclohexanone), and enantioselectivity up to 71% ee. Trifluoroacetic acid and benzoic acid proved to be the best cocatalysts for the aldol process on 4-nitrobenzaldehyde and isatin, respectively.

Název v anglickém jazyce

Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions

Popis výsledku anglicky

A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared amines were screened as organocatalysts in the direct asymmetric aldol reaction between 4-nitrobenzaldehyde or isatin and acetone or cyclohexanone. The aldol adducts were obtained in good chemical yields, diastereoselectivity¬ up to 97:3 (reactions with cyclohexanone), and enantioselectivity up to 71% ee. Trifluoroacetic acid and benzoic acid proved to be the best cocatalysts for the aldol process on 4-nitrobenzaldehyde and isatin, respectively.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

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

7

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

1613-1622

Kód UT WoS článku

000398467400018

EID výsledku v databázi Scopus

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