Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center

Popis výsledku v původním jazyce

Azlactone is an important starting material for synthesizing amino acids containing a quaternary alpha-carbon. In this study, we have developed a sequential &quot;one-pot&quot; 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.

Název v anglickém jazyce

Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center

Popis výsledku anglicky

Azlactone is an important starting material for synthesizing amino acids containing a quaternary alpha-carbon. In this study, we have developed a sequential &quot;one-pot&quot; 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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

89

Číslo periodika v rámci svazku

22

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

16522-16530

Kód UT WoS článku

001344911500001

EID výsledku v databázi Scopus

2-s2.0-85208272996