Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39902351" target="_blank" >RIV/00216275:25310/17:39902351 - isvavai.cz</a>
Result on the web
<a href="https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588107" target="_blank" >https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588107</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1055/s-0036-1588107" target="_blank" >10.1055/s-0036-1588107</a>
Alternative languages
Result language
angličtina
Original language name
Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Synthesis
ISSN
0039-7881
e-ISSN
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Volume of the periodical
49
Issue of the periodical within the volume
7
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
1613-1622
UT code for WoS article
000398467400018
EID of the result in the Scopus database
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