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

Sakamoto, Daisuke; Gay Sánchez, Isabel; Rybáček, Jiří; Vacek, Jaroslav; Bednárová, Lucie; Pazderková, Markéta; Pohl, Radek; Císařová, I.; Stará, Irena G.; Starý, Ivo

doi:https://dx.doi.org/10.1021/acscatal.2c01816

Number of the records: 1

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

1.

SYSNO ASEP	0561135
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines
Author(s)	Sakamoto, Daisuke (UOCHB-X) Gay Sánchez, Isabel (UOCHB-X)_{RID, ORCID} Rybáček, Jiří (UOCHB-X)_{RID, ORCID} Vacek, Jaroslav (UOCHB-X)_{RID, ORCID} Bednárová, Lucie (UOCHB-X)_{RID, ORCID} Pazderková, Markéta (UOCHB-X)_{RID, ORCID} Pohl, Radek (UOCHB-X)_{RID, ORCID} Císařová, I. (CZ) Stará, Irena G. (UOCHB-X)_{RID, ORCID} Starý, Ivo (UOCHB-X)_{RID, ORCID}
Source Title	ACS Catalysis. - : American Chemical Society - ISSN 2155-5435 Roč. 12, č. 17 (2022), s. 10793-10800
Number of pages	8 s.
Language	eng - English
Country	US - United States
Keywords	helicenes ; iridacycles ; asymmetric transfer hydrogenation ; imines ; chirality
OECD category	Organic chemistry
R&D Projects	GA19-10144S GA ČR - Czech Science Foundation (CSF)
Method of publishing	Limited access
Institutional support	UOCHB-X - RVO:61388963
UT WOS	000851399600001
EID SCOPUS	85137277486
DOI	10.1021/acscatal.2c01816
Annotation	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 auxiliary helix rather than the IrIII stereogenic center of the chiral iridacycles.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
Year of Publishing	2023
Electronic address	https://doi.org/10.1021/acscatal.2c01816

Number of the records: 1