Hydrogen-bonding ability of Noyori–Ikariya catalysts enables stereoselective access to CF[sub]3-substituted syn-1,2-diols via dynamic kinetic resolution

Maša Sterle (Avtor), Matej Huš (Avtor), Matic Lozinšek (Avtor), Anamarija Zega (Avtor), Andrej Emanuel Cotman (Avtor)

Povzetek

Stereopure CF[sub]3-substituted syn-1,2-diols were prepared via the reductive dynamic kinetic resolution of the corresponding racemic α-hydroxyketones in HCO[sub]2H/Et[sub]3N. (Het)aryl, benzyl, vinyl, and alkyl ketones are tolerated, delivering products with ≥95% ee and ≥87:13 syn/anti. This methodology offers rapid access to stereopure bioactive molecules. Furthermore, DFT calculations for three types of Noyori–Ikariya ruthenium catalysts were performed to show their general ability of directing stereoselectivity via the hydrogen bond acceptor SO[sub]2 region and CH/π interactions.

Ključne besede

asymmetric catalysis;DFT;drug design;fluorine;hydrogenation;kinetic resolution;ruthenium;

Podatki

Jezik:	Angleški jezik
Leto izida:	2023
Tipologija:	1.03 - Kratki znanstveni prispevek
Organizacija:	UL FFA - Fakulteta za farmacijo
UDK:	544.4
COBISS:	150693379
ISSN:	2155-5435
Št. ogledov:	61
Št. prenosov:	8
Ocena:	0 (0 glasov)
Metapodatki:

Ostali podatki

Sekundarni jezik:	Slovenski jezik
Sekundarne ključne besede:	asimetrična kataliza;oblikovanje zdravil;fluor hidrogenacija;kinetična ločljivost;rutenij;Kemijska kinetika;
Vrsta dela (COBISS):	Članek v reviji
Strani:	str. 6242-6248
Zvezek:	ǂVol. ǂ13
Čas izdaje:	2023
DOI:	10.1021/acscatal.3c00980
ID:	19406742