Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00561135" target="_blank" >RIV/61388963:_____/22:00561135 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/22:10448845

Výsledek na webu

<a href="https://doi.org/10.1021/acscatal.2c01816" target="_blank" >https://doi.org/10.1021/acscatal.2c01816</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscatal.2c01816" target="_blank" >10.1021/acscatal.2c01816</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines

Popis výsledku v původním jazyce

The asymmetric synthesis of optically pure and conformationally locked oxabenzo[5]helicenes bearing pyridin-2-yl or isoquinolin-3-yl substituents and their transformation into the corresponding cycloiridated organometallics are described. These helically chiral Cp*IrIII(X)C,N-complexes (X = Cl, I) also contain a configurationally unstable pseudotetrahedral iridium center. This center undergoes epimerization at room temperature, and its relative stereochemistry, especially in the solid state, depends on the nature of the coordinated ligands. Cycloiridated helicenes were used in the asymmetric transfer hydrogenation of prochiral aromatic imines with formic acid/triethylamine to reach up to 96:4 er. It is assumed that the chirality transfer is controlled by the auxiliarynhelix rather than the IrIII stereogenic center of the chiral iridacycles.

Název v anglickém jazyce

Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines

Popis výsledku anglicky

The asymmetric synthesis of optically pure and conformationally locked oxabenzo[5]helicenes bearing pyridin-2-yl or isoquinolin-3-yl substituents and their transformation into the corresponding cycloiridated organometallics are described. These helically chiral Cp*IrIII(X)C,N-complexes (X = Cl, I) also contain a configurationally unstable pseudotetrahedral iridium center. This center undergoes epimerization at room temperature, and its relative stereochemistry, especially in the solid state, depends on the nature of the coordinated ligands. Cycloiridated helicenes were used in the asymmetric transfer hydrogenation of prochiral aromatic imines with formic acid/triethylamine to reach up to 96:4 er. It is assumed that the chirality transfer is controlled by the auxiliarynhelix rather than the IrIII stereogenic center of the chiral iridacycles.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA19-10144S" target="_blank" >GA19-10144S: Enantioselektivní katalýza kontrolovaná helikální chiralitou</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

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

Název periodika

ACS Catalysis

ISSN

2155-5435

e-ISSN

2155-5435

Svazek periodika

12

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

8

Strana od-do

10793-10800

Kód UT WoS článku

000851399600001

EID výsledku v databázi Scopus

2-s2.0-85137277486