Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10487800" target="_blank" >RIV/00216208:11310/24:10487800 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=V1BJYVSkml" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=V1BJYVSkml</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.4c01764" target="_blank" >10.1021/acs.joc.4c01764</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center
Original language description
Azlactone is an important starting material for synthesizing amino acids containing a quaternary alpha-carbon. In this study, we have developed a sequential "one-pot" procedure involving an enantioselective spirocyclization reaction followed by acidic azlactone opening, which led to amino acid derivatives. The key step of this procedure is a spirocyclization between propargylated azlactones and enals by using a cooperative catalytic approach that combines chiral secondary amine and achiral Pd(0) complexes. The final acid opening of the azlactone motif allows isolation of the corresponding amino acid derivatives as major diastereoisomers in yields ranging from 37% to 70% with enantioselectivities of 85-97% ee. These synthesized amino acid derivatives hold great potential in the pharmaceutical and bioactive compound industries. Moreover, the final amino acid products with a cyclopentene moiety can be further derivatized, opening up even more possibilities for their application.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
89
Issue of the periodical within the volume
22
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
16522-16530
UT code for WoS article
001344911500001
EID of the result in the Scopus database
2-s2.0-85208272996