Lithium Chloride Catalyzed Asymmetric Domino Aza-Michael Addition/[3+2] Cycloaddition Reactions for the Synthesis of Spiro- and Bicyclic α,β,γ-Triamino Acid Derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495773" target="_blank" >RIV/61388963:_____/18:00495773 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201800585" target="_blank" >http://dx.doi.org/10.1002/ejoc.201800585</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201800585" target="_blank" >10.1002/ejoc.201800585</a>
Alternative languages
Result language
angličtina
Original language name
Lithium Chloride Catalyzed Asymmetric Domino Aza-Michael Addition/[3+2] Cycloaddition Reactions for the Synthesis of Spiro- and Bicyclic α,β,γ-Triamino Acid Derivatives
Original language description
Angularly and peri-fused tricyclic pyrrolidinopyrazolines are efficiently prepared by LiCl-catalyzed domino aza-Michael addition-1,3-dipolar cycloaddition reactions. The absolute stereochemistry is controlled in the aza-Michael addition step, nonaflyl azide serves as effective diazo transfer reagent to the formed enolate and the resulting diazo dipole engages in the 1,3-dipolar cycloaddition step. The resulting tricyclic pyrrolidinopyrazolines can be easily transformed to enantiomerically enriched nonproteinogenic spirocyclic α,β,γ-triamino acids, angularly or peri-fused tricyclic β-prolines or pyrimidines. The activity of the tricyclic amino acid derivatives against the hepatitis C virus was determined.
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
<a href="/en/project/EF16_019%2F0000729" target="_blank" >EF16_019/0000729: Chemical biology for drugging undruggable targets</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2018
Issue of the periodical within the volume
37
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
5213-5221
UT code for WoS article
000446662900015
EID of the result in the Scopus database
2-s2.0-85053068094